氨基酸衍生物席夫碱稀土配合物合成及催化性能研究
|
摘要
稀土金属离子由于d和f轨道的存在而具有4到12的各种配位数,容易与多种配体形成结构各异的配合物。其中稀土元素与氨基酸席夫碱配体形成的配合物具有多样的稳定结构和良好的生物活性、光学特性,并在催化及功能材料等领域都有广泛的应用前景。
氨基酸是人体蛋白质等与生命有关的基本物质,氨基酸及其衍生物具有较低的毒性和耐药性;同时,它又是天然的廉价手性源,可应用于多种有机反应的不对称催化。
环状碳酸酯是由二氧化碳化学固定得到的,作为中间体和极性有机溶剂具有广泛应用价值,可应用于有机合成、气体分离、电池介电质及金属萃取等领域。本研究小组近年来致力于研究环状碳酸酯的手性和非手性合成,并建立了多种手性和非手性催化体系。本文由母配体二-(3,5-二特丁基水杨醛缩胺乙基)氨(H_2L)}和不同手性氨基酸衍生物反应合成了未见文献报道的六种手性席夫碱配体(H_2L~1～H_2L~5,H_3L~6),再与LaCl_3·7H_2O配位合成相应的稀土镧配合物;用核磁共振光谱、红外光谱、质谱和元素分析对配体及其配合物进行了表征。最后考察了稀土催化剂对环氧化合物和二氧化碳的偶联反应的催化性能,其结果为下一步工作指出明确的方向,从而进一步了解物质性质与其结构的密切联系。
Rare earth metal ions have 4 to 12 coordination number for the existence of d and f orbits,the complexes are easily synthesized from coordination of rare earth metal and multiplicate ligands.Among them,the lanthanide complexes with amino acid Schiff bases,which have various stable structures and the vital bioactivity and excellent luminescence,were widely used in the fields of catalysis and material etc.
Amino acids are the basic unit of composition of the materials of life,amino acids and their derivatives with low toxicity and resistance are widely applied to chiral catalysis of various oganic reactions as natural and cheap chiral resource.
Cyclic carbonates attained by chemical fixation of CO_2 are applied to the fields of oganic synthesis,gas separation,battery electromedium,metal extraction etc as chemical intermediate and polar organic solvent.In recent years,our group has been studying on symmetric and asymmetric synthesis of cyclic carbonates and the establishment of a variety of chiral and achiral catalytic systems.In my paper,eight new chiral schiff base ligands(H_2L~1～H_2L~5,H_3L~6)were synthesized by the reaction of the mother ligand[(2-OH-3,5-di-~(t-)Bu-C_6H_2)CH=NCH_2CH_2]_2NH(H_2L)with the chiral amino acid derivatives,their lanthanide complexes prepared from the coordination of the ligands and Lanthanum compound(LaCl_3·7H_2O);The ligands and their lanthanide complexes were characterized by nuclear magnetic resonance, mass spectrometry、infrared spectroscopy and elemental analysis.Finally the catalytic properties of the complexes were studied on the coupling reaction of the epoxides and CO_2,and the results clearly pointed out what the next step of our work is.It made us further understanding affinity of material properties and structure.
氨基酸是人体蛋白质等与生命有关的基本物质,氨基酸及其衍生物具有较低的毒性和耐药性;同时,它又是天然的廉价手性源,可应用于多种有机反应的不对称催化。
环状碳酸酯是由二氧化碳化学固定得到的,作为中间体和极性有机溶剂具有广泛应用价值,可应用于有机合成、气体分离、电池介电质及金属萃取等领域。本研究小组近年来致力于研究环状碳酸酯的手性和非手性合成,并建立了多种手性和非手性催化体系。本文由母配体二-(3,5-二特丁基水杨醛缩胺乙基)氨(H_2L)}和不同手性氨基酸衍生物反应合成了未见文献报道的六种手性席夫碱配体(H_2L~1～H_2L~5,H_3L~6),再与LaCl_3·7H_2O配位合成相应的稀土镧配合物;用核磁共振光谱、红外光谱、质谱和元素分析对配体及其配合物进行了表征。最后考察了稀土催化剂对环氧化合物和二氧化碳的偶联反应的催化性能,其结果为下一步工作指出明确的方向,从而进一步了解物质性质与其结构的密切联系。
Rare earth metal ions have 4 to 12 coordination number for the existence of d and f orbits,the complexes are easily synthesized from coordination of rare earth metal and multiplicate ligands.Among them,the lanthanide complexes with amino acid Schiff bases,which have various stable structures and the vital bioactivity and excellent luminescence,were widely used in the fields of catalysis and material etc.
Amino acids are the basic unit of composition of the materials of life,amino acids and their derivatives with low toxicity and resistance are widely applied to chiral catalysis of various oganic reactions as natural and cheap chiral resource.
Cyclic carbonates attained by chemical fixation of CO_2 are applied to the fields of oganic synthesis,gas separation,battery electromedium,metal extraction etc as chemical intermediate and polar organic solvent.In recent years,our group has been studying on symmetric and asymmetric synthesis of cyclic carbonates and the establishment of a variety of chiral and achiral catalytic systems.In my paper,eight new chiral schiff base ligands(H_2L~1～H_2L~5,H_3L~6)were synthesized by the reaction of the mother ligand[(2-OH-3,5-di-~(t-)Bu-C_6H_2)CH=NCH_2CH_2]_2NH(H_2L)with the chiral amino acid derivatives,their lanthanide complexes prepared from the coordination of the ligands and Lanthanum compound(LaCl_3·7H_2O);The ligands and their lanthanide complexes were characterized by nuclear magnetic resonance, mass spectrometry、infrared spectroscopy and elemental analysis.Finally the catalytic properties of the complexes were studied on the coupling reaction of the epoxides and CO_2,and the results clearly pointed out what the next step of our work is.It made us further understanding affinity of material properties and structure.
引文
[1]陈长虹,鲍仙华.全球能源消费与CO_2排放量.上海环境科学,1999,18(2):62-64.
[2]李昆瑜.CO_2的应用及产品开发.天然气化工(C 化学与化工),1996,21(3):40-43.
[3]周忠清.二氧化碳催化还原成碳的发展.精细石油化工,1994,(4):92-96
[4]李淑芬,陈宝良,韩金玉.超临界CO_2萃取天然产品的特性研究.化工进展,1997,(2):10-14.
[5]谈士海,张文正.非混相CO_2驱油在油田增产中的应用.石油钻探技术,2001,29,(2):58-59.
[6]Aresta M..Perspectives of Carbon Dioxide Utilisation In the Synthesis of Chemicals Coupling Chemistry with Biotechnology.Stud.Surf.Sci.Catal.,1998,114:65-76.
[7]梁斌.CO_2与环氧丙烷不对称环加成反应催化体系的设计与研究[D].大连理工大学硕士学位论文,2004.3.
[8]Dean C.W..Cyclic Carbonate Functional Polymers and Their Applications.Progr.Org.Coat.,2003,47(1):77-86.
[9]Alicja.W.,Lech C..A Comparison of Acid-Base Properties of Substituted Pyridines and Their N-Oxides in Propylene Carbonate.J.Chem.Thermodynamics.,1998,30(6):713-722.
[10]Wei T.,Wang M.,Wei W.,Sun Y.H.,Zhong B..Effect of Base Strength and Basicity on Catalytic Behavior of Solid Bases for Synthesis of Dimethyl Carbonate from Propylene Carbonate and Methanol.Fuel.Process.Technol.,2003,83(1-3):175-182.
[11]宝中明秀.碳酸丙烯醋复合溶剂研究.化学工程,1999,27(2):51-53.
[12]Le Q.H.,Yan S.,Tu J.L..A New Complex Absorbent Used for Improving Propylene Carbonate Absorbent for Carbon Dioxide Removal.Sep.Purif.Technol.,1999,16(2):133-138.
[13]陈卫祥,杨兰生,单志强,邹建梅,刘黎.全固态锂电池用聚合物电解质的 研究.电源技术,1996.20(2):50-54.
[14]Wolfenstine.J.,Shictman M.,Read J.,Foster D.,Behl W..The Effect of the Mn-Ion Oxidation State on Propylene Carbonate Decomposition.J.Power Sources,2000,91(2):118-121.
[15]朱宏,陈立班,江英彦.均相催化剂催化合成碳酸丙烯酯.天然化工(C1化学与化工),1997,22(1):9-11.
[16]陶洪连,黄敏.碳酸丙烯酯脱碳装置技术改造小结.化学工业与工程技术,2002,23(5):27-29.
[17]Hou X.P.,Kok S.Ionic Conductivity and Electrochemical Characterization of Novel Interpenetrating Polymer Network Electrolytes.Solid State Ionics,2002,147(3-4):391-395.
[18]Behr A..Carbon Dioxide Activation by Metal Complex.New York:VCH Publishers.1988,91-93.
[19]Rokicki A.,Kuran W.,Marcinick B.P..Cyclic Carbonates from Carbon Dioxide and Oxiranes.Monatsch.Chem.,1984,115(2):205-214.
[20]江琦,黄仲涛.CO_2与环氧丙烷环加成的催化剂及反应工艺研究.天然气化工(C 化学与化工),1996,21(6):2-24
[21]Kihara N.,Hara N.,Endo T..Catalytic Activity of Various Salts in the Reaction of 2,3-Epoxypropyl Phenyl Ether and Carbon Dioxide under Atmospheric Pressure.J.Org.Chem.,1993,58(23):6198-6202.
[22]Krasimir K.,Neli K.,Kolio T..Calcium Chloride as Co-Catalyst of Onium Halides in the Cycloaddition of Carbon Dioxide to Oxiranes.J.Mol.Catal.,A:Chem.,2003,194:29-37.
[23]Nishikubo T.,Kameyama A.,Yamashita J.,Tomoi M.,Fukuda W..Insoluble Polystyrene-Bound Quaternary Onium Salt Catalysts for the Synthesis of Cyclic Carbonates by the Reaction of Oxiranes with Carbon Dioxide.J.Polym.Sci.,Part A:Polymer.Chem.,1993,31(4):939-947.
[24]Matsuda H.,Ninagawa A.,Nomura R..Reaction of Carbon Dioxide with Epoxides in the Presence of Pentavalent Organoantimony Compounds.Chem.Lett.,1979,(2):1261-1262.
[25] Nomura R., Ninagawa A., Matsuda H.. Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides in the Presence of Organoantimony Compounds as Novel Catalysts. J. Org. Chem., 1980,45(19): 3735-3738.
[26] Nomura R., Kimura M., Ninagawa A., Matsuda H.. Direct Synthesis of Cyclic Carbonates in the Presence of Organometallic Compounds. Catalyses of Systems from Group IVA, VA, and VIA Compounds and A Lewis Base. Bull. Chem. Soc. Jpn., 1982, 55(10): 3200-3203.
[27] Baba A., Nozaki T., Matsuda H.. Carbonate Formation from Oxiranes and Carbon Dioxide Catalyzed by Organotin Halide-Tetraalkylphosphonium Halide Complexes. Bull. Chem. Soc Jpn., 1987,60(4): 1552-1554.
[28] Jing H. W., Smita K. E., Julianne M. G., Charlotte L. S., Hongying Zhou.. (Salen)Tin Complexes: Syntheses, Characterization, Crystal Structures, and Catalytic Activity in the Formation of Propylene Carbonate from CO_2 and Propylene Oxide. Inorg. Chem. 2004,43(14): 4315-4327.
[29] Gupta M. K., Singh H. L., Tripaathi U. D., Varshney A. K.. Bull.Pol. Acad. Sci. Chem. 2000,48,195-201.
[30] Atwood D. A., Jegier J. A., Martin K. J., Rutherford D.. J. Organomet. Chem. 1995, 503, C4-C7.
[31] Paddock R. L., Nguyen S. T.. Chemical CO_2 Fixation: Cr(III) Salen Complexes as Highly Efficient Catalysts for the Coupling of CO_2 and Epoxides. J. Am. Chem. Soc. 2001,123(46): 11498-11499.
[32] Jing H.W., SonBinh T. Nguyen.. SnCl_4-organic Base: Highly Efficient Catalyst System for Coupling Reaction of CO_2 and Epoxides. J. Mol. Catal. A: Chem., 2007, 261(1): 12-15.
[33] Kim H. S., Kim J. J., Lee S. D., Lah M. S..New Mechanistic Insight into the Coupling Reactions of CO_2 and Epoxides in the Presence of Zinc Complexes. Chem. Eur. J. 2003, 9(3): 678-686.
[34] Allen S.D., Moore D.R., Lobkovsky E. B.. High-Activity Single- Site Catalysts for the Alternating Copolymerization of CO_2 and Propylene Oxide. J. Am.Chem. Soc, 2002,124(48): 14284-14285.
[35]Kim J.S.,Re.e.M.,Shin T.J.,Han.O.H.,Cho.S.J.,Hwang Y.-T..X-Ray Absorption and NMR Spectroscopic Investigations of Zinc Glutarates Prepared from Various Zinc Sources and Their Catalytic Activities in the Copolymerization of Carbon Dioxide and Propylene Oxide.J.Catal.,2003,218(1):209-219.
[36]Quan Z.,Wang X.H.,Zhao X.J.,Wang F S..Copolymerization of CO_2 and Propylene Oxide under Rare Earth Ternary Catalyst:Design of Ligand in Yttrium Complex.Polymer,2003,44(19):5605-5610
[37]Kisch H.,Millini R.,Wang L..Bifunktionelle Katalysatoren zur Synthese cyclischer Carbonate aus Oxiranen and Kohlendioxid.Chem.Ber.,1986,119:1090-1093.
[38]Dumlei.W,Kisch.H..Bifunktionelle Katalyse der Reaktion von Kohlendioxid mit Oxiranen.Chem.Ber,1990,123:277-283.
[39]常涛,吴梅,靳丽丽,景欢旺,邱文元.溴化锌-季鎓三溴盐催化二氧化碳和环氧化合物偶联反应.催化学报,2007,28(5):404-406.
[40]Tao Chang,Huanwang Jing,Lili Jin,Wenyuan Qiu.Quaternary Onium Tribromide Catalyzed Cyclic Carbonate Synthesis from Carbon Dioxide and Epoxides.J.Mol.Catal.A:Chem.,2007,264(1-2):241-247.
[41]Kim H.S.,Kim J.J.,Le.e.B.G.,Jung O.S.,Jang H.G.,Kang S.O..The First Isolation of Pyridinium Alkoxy Ion-bridged Dimeric Zinc Complex for the Coupling Reaction of CO_2 and Epoxides.Angew.Chem.Int.Ed.Engl.,2000,39:4096-4098.
[42]Hoon S.K,Jai K.,Honggon K.,Ho G.J.,Ho G J..Well-Defined Highly Active Heterogeneous Catalyst System for the Coupling Reactions of Carbon Dioxide and Epoxides.,J.Catal.,2002,205(1):226-229.
[43]Hoon.S.K,Jai.K.,Honggon.K.,Ho.G..J..Imidazolium Zinc TetrahalideCatalyzed Coupling Reaction of CO_2 and Ethylene Oxide or Propylene Oxide.J.Catal.,2003,220(1):44-46.
[44]Ralph J.D.P..Unusual Catalysis With Nickel(0)Complexes.J.C.S.,Chem.Comm.,1973,(5):157-158.
[45]Jan E.B.,Ola K.Stig O.L..Stereochemistry of Copper- and NickelCatalyzed Insertion of Carbon Dioxide into Epoxides.A Microwave Study.Tetrahedron Lett.,1980,21(51):4985-4988.
[46]Fujinami T.,Suzuki T.,Kamiya M.,Fuzawa S.,Sakai S..Palladium Catalyzed Reaction of Butadiene Monoxide with Carbon Dioxide.Chem.Lett.,1985,(2):199-200.
[47]Trost B.M.,Angle A.R..Palladium-Mediated Vicinal Cleavage of Ally1Epoxides With Retention of Stereochemistry:A Cis Hydroxylation Equivalent.J.Am.Chem.Soc.,1985,107(21):6123-6124.
[48]Hiroyuki Y.,H.L.-N.,Toshiyasu S..Cyclic Carbonate Synthesis from Supercritical Carbon Dioxide and Epoxide over Lanthanide Oxychloride.J.Catal.,2002,209:547-550.
[49]Lili Jin,Huanwang Jing,Tao Chang,Xiuli Bu,Li Wang,Zhongli Liu..Metal Porphyrin/Phenyltrimethylammonium Tribromide:High Efficient Catalysts for Coupling Reaction of CO_2 and Epoxides.J.Mol.Catal.A:Chem.,2007,261(2):262-266.
[50]靳丽丽,常涛,景欢旺.钌卟啉络合物催化二氧化碳与环氧化合物偶联反应.催化学报,2007,28(4):287-289.
[51]Michael R.,Fabian J.,Grunwaldt J.D.,Alfons B..Solventless synthesis of propylene carbonate eatalysed by chromium-salen complexes:Bridging homogeneous and heterogeneous catalysis.J.Mol.Catal.A:Chem.,2005,242(1-2):32-39.
[52]Miao C.X.,Wang J.Q.,Wu Y.,Du Y.,He L.N..Bifunctional Metal-Salen Complexes as Efficient Catalysts for the Fixation of CO_2 with Epoxides under Solvent-Free Conditions.ChemSusChem,2008,1,236-241.
[53]Michele A,Angela D.,Libero G.,Carlo P..Nb(V)Compounds as Epoxides Carboxylation Catalysts:the Role of the Solvent.J.Mol.Catal.A:Chem.,2003,204-205:245-252.
[54]Hiroyuki Y.,H.L.-N,Toshiyasu S..Cyclic Carbonate Synthesis from Supercritical Carbon Dioxide and Epoxide over Lanthanide oxychloride.J. Catal.,2002,209(2):547-550.
[55]Welton T..Room-Temperature Ionic Liquids.Solvents for Synthesis and Catalysis.Chem.Rev.1999,99(8):2071-2084.
[56]Zhao D.,Wu M..Kou Y,Min E..Ionic liquids:applications in catalysis.Catal.Today.,2002,74(1-2):157-189.
[57]彭家建,邓友全.室温离子液体催化合成碳酸丙烯酯.催化学报,2001,22(6):598-600.
[58]Hajime A.,Akiyoshi A.,Keitaro A.,Yutaka K..A Rapid and Effective Synthesis of Propylene Carbonate Using a Supercritical CO_2 Onic Liquid System.Chem.Commun.,2003,(7):896-897.
[59]Qi C.R.,Jiang H.F.,Wang Z.Y.,Zou B.,Yang S.R..Naturally Occurringamino Acid-catalyzed Coupling of Carbon Dioxide with Epoxides to Afford Cyclic Carbonates.Synlett.,2007,(2):255-258.
[60]Alessandro B.,Raimondo M.,Alessandro M.,Giovanni M.,Giovanni S.,Raffaella S..Cycloaddition of CO_2 to Epoxides over Both Homogeneous and Silica-supported Guanidine Catalysts.Tetrahedron Lett.,2003,44(14):2931-2934.
[61]Takashi Y.,Hideo M.,Takahiro K.,Hiroyasu L.,Hisashi F.,Masakuni Y.Toshihisa M..Magnesium Oxide-catalysed Reaction Of Carbon Dioxide with an Epoxide Withretention Of Stereochemistry.Chem.Commun.,1997,(12):1129-1130.
[62]Yamaguchi K.,Ebitani K.,Yoshida T.,Yoshida H.,Kaneda K..Mg-A1 Mixed Oxides as Highly Active Acid-Base Catalysts for Cycloaddition of Carbon Dioxide to Epoxides.J.Am.Chem.Soc.,1999,121(18):4526-4527.
[63]Sorana L.,Katherine W.,Mandelin P.,Benny A.,Rick W..Geometric Requirements for the Photolysis of Aryloxiranes and Cyclic Carbonate.Tetrahedron Lett.,2002,43(7):1169-1170.
[64]Hiroyuki U.,Motomu K.Masakatsu S..Studies toward the Total Synthesis of Garsubellin A:Synthesis of 8-depreny1-garsubellin A.Tetrahedron Lett.,2002,43(20):3621-3624.
[65] Jegham S., Nedelec A., Bumier P., Guminski Y., Puech F., Koenig J.J., George P.. Use of Chiral Glycerol 2,3-Carbonate in the Synthesis of 3-Aryl-2-oxazolidinones. Tetrahedron Lett., 1998, 39(25): 4453-4454.
[66] Kolb H.C., VanNieuwenhze M.S., Sharpless K.B.. Catalytic Asymmetric Dihydroxylation. Chem. Rev., 1994, 94(8): 2483-2547.
[67] Scott E. S., Bridget D. B., Jay F. L., Makoto T., Karl B. H., Alexandra E.G.. Highly Selective Hydrolytic Kinetic Resolution of TerminalEpoxides Catalyzed by Chiral (salen)Co(III) Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2- Diols. J. Am. Chem. Soc, 2002, 124(7): 1307-1315.
[68] Patrick B. Michael L. P. The Resolution of Racemic 1,2-diols By the Esterase Catalysed Hydrolysis of The Corresponding Cyclic Carbonate. Tetrahedron, 1992,48(36): 7731-7734.
[69] Srinivasan K, Michaud P, Kochi J. K.. Epoxidation of Olefins with Cationic (salen)manganese(III) Complexes. The Modulation of Catalytic Activity by Substituents. J. Am. Chem. Soc,1986,108(9): 2309- 2320.
[70] Katsuki T. Mn-salen Catalyst, Competitor of Enzymes, for Asymmetric Epoxidation. J. Mol. Cat. A, 1996,113(1-2): 87-107.
[71] Fukuda T., Katsuki T.. Highly Enantioselective Cyclopropanation of Styrene Derivatives Using Co(III)-Salen Complex as a Catalyst. Tetrahedron, 1997, 53(21): 7201-7208.
[72] Tokunaga M , L arrow J F, Jacobsen E N. Asymmetric Catalysis with Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis. Science,1997,277: 936-938.
[73] Masutani K, Uchida T, Irie R, Katsuki T. Catalytic Asymmetric and Chemoselective AerobicOxidation: Kinetic Resolution of Sec-alcohols. Tetrahedron. Lett, 2000,41(26): 5119-5123.
[74] Lu X. B., Liang B., Zhang Y. J., e tal. Asymmetric Catalysis with CO_2: Direct Synthesis of Optically Active Propylene Carbonate from Racemic Epoxides. J. Am. Chem. Soc, 2004,126(12): 3732-3733.
[75]Paddock R.T.,Nguyen S.T.,Chiral(salen)Co~Ⅲ catalyst for the synthesis of cyclic carbonates.Chem.Commun.,2004,1622-1623.
[76]Berkessel,A.,Brandenburg,M..Catalytic Asymmetric Addition of Carbon Dioxide to Propylene Oxide with Unprecedented Enantioselectivity.Org.Lett.2006,8(20):4401-4404.
[77]S.W.Chen,Kawtherkar R.B.,G J.Kim..One-pot combination of the Wittig olefination with oxidation,hydrogenation,bromination,and photocyclization reactions.Tetrahedron Lett.,2007,48(2):293.
[78]H.Tanaka.,Y.Kitaich.i,M.Sato.,T.Ikeno,T.Yamada..Enantioselective CO_2Fixation Catalyzed by Optically Active Cobalt Complexes.Chem.Lett.2004,33(6):676.
[79]W.Yamada.,Y.Kitaichi,H.Tanaka,T.Kojima,M.Sato,T.Ikeno,T.Yamada..Enantioselective Incorporation of Carbon Dioxide into Epoxides Catalyzed by Optically Active Cobalt(Ⅱ)Complexes.Bull.Chem.Soc.Jpn.2007,80(7):1391.
[80]卢毅.稀土schiff碱配合物的合成及催化环酯开环聚合[D],浙江大学硕士学位论文,2007.5.
[81]Yang Haijian,Sun Wenhan,Li Zilong,Ma Zhi.The Rapid Synthesis of /Schiff- Base without Solvent under Microwave Irradiation.Chin.Chem.Lett.,2002,13(1):3-6.
[82]Bernhardt P.V.,Bernadine M.F.,Mark J.R..Isomorphous Lanthanide Complexes of a Tripodal N_4O_3 Ligand.Aust.J.Chem.,2000,53,229-231.
[83]Bernhardt P.V.,Flanagan.B.M.,Riley.M.J..Completion of the Isomorphous Ln(trensal)Series.Aust.J.Chem.2001,54,229-232.
[84]Michael W.E.,D.Webster Keogh.,Brian L.Scott,John G.Watki..Synthesis and Structural Characterization of the Lanthanide Schiff-Base Complexes {N[CH_2CH_2N=CH(2-O-3,5-t-Bu_2C_6,H_2)]3} Ln(Ln=Sm,Nd),Polyhedron,2001,20(5):373-377.
[85]马红竹,手性镧系配合物的合成、表征及不对称催化性质研究[D].西北大 学博士学位论文,2005.3.
[86]Carmona D.,Lamata M.P.,Oro L.A..Recent Advances In Homogeneous Enantioselective Dieis-Alder Reactions Catalyzed by Chiral TransitionMetal Complexes.,Coord Chem.Chem.,2000,200-202,717-772.
[87]Shinya K.,Hirofumi Nakano,Masaaki K.,Naomichi B.,Kiyohiko N..An effect of the ionic radii of lanthanide(Ⅲ)ions on the structure andcatalytic properties of chiral Schiff base-lanthanide(Ⅲ)complexes.Inorganica.Chimica.Acta.,2003,349(5):6-16.
[88]张伟国等.氨基酸生产技术及其应用[M].中国轻工业出版社,北京:1997
[89]LI JingWei,XU LiWen,XIA ChunGu.Advances in Proline-Catalyzed Asymmetric Reactions.Chin.J.Org.Chem.,2004,24(1):23-28.
[90]Huang J.L.,Liu X.H.,Wen Y.H.,Bo Qin,Feng X.M..Enantioselective Strecker Reaction of Phosphinoyl Ketoimines Catalyzed by in Situ Prepared Chiral N,N-Dioxides.J.Org.Chem.,2007,72(1):204-208.
[91]李宁,姚克敏,楼开炎等,La(Ⅲ),Y(Ⅲ)与多甘醇醛缩氨基酸Schiff碱配合物的合成及其固体高分辨-(13)CNMR波谱.中国科学,B辑,1999,29(5):450-455.
[1](a)Mizukami S,Houjou H,Kanesato M,et al.Adjustment of Twist Angles in Pseudo-Helical Lanthanide Complexes by the Size of Metal Ions.Chem.Eur.J.2003,9(7):1521-1528.
(b)Essig M.W,Keogh D.W,Scott B.L,et al.Synthesis and structural characterization of the lanthanide Schiff-base complexes {N[CH_2CH_2N=CH(2-O-3,5-tert-BuC_6H_2)]3}Ln(La,Sm,Nd)[J].Polyhedron,2001,20(5):373-377.
[2](a)Kano S.,Nakano H..An Effect of The Ionic Radii of Lanthanide(Ⅲ)Ions on the Structure and Catalytic Properties of Chiral Schiff Base-Lanthanide(Ⅲ)Complexes.Inorganica Chimica.,Acta,2003,349(5):6-16.
(b)Carmona D,Lamata M.P.,Oro L.A..Recent Advances In Homogeneous Enantioselective Diels-Aider Reactions Catalyzed by Chiral Transition-Metal Complexes,Coord.Chem.Rev.,2000,200-202,717-772.
[3](a)Han Zhi-jian,Wang Rui,Zhou Yi-feng,et al.Simple Derivatives of Natural Amino Acids as Chiral Ligands in the Catalytic Asymmetric Addition of Phenylacetylene to Aldehydes,Eur.J.Org.Chem.,2005,2005(5):934-938.
(b)Traverse J.F.,Yu Zhao,Hoveyda A.H.,et al,Proline-Based N-Oxides as Readily Available and Modular Chiral Catalysts.Enantioselective Reactions of Allyltrichlorosilane with Aldehydes.Org.Let.,2005,7(15):3151-3154.
(c)魏丹毅,李冬成,姚可敏等.稀土元素与丙氨酸SChiff碱双核配合物的合成与表征及催化活性.无机化学学报,1998,14(2):209-214.
[4](a)Chang Tao,Jing Huanwang,Jin Lili et al.Quaternary Oninm Tribromide Catalyzed Cyclic Carbonate Synthesis from Carbon Dioxide and Epoxides.J.Mol.Catal.A:Chem.,2007,264(1-2):241-247.
(b)Jin L.I.,Jing H.W.,Chang T.et al..Metal Porphyrin/phenyltrimethyltribromide:High Efficient Catalysts for Coupling Reaction of CO_2 and Epoxides.J.Mol.Catal.A:Chem.,2007,261(1-2):262-266.
(c)Jing H.W.,Edulji S.K.,Nguyen S.T.et al.(Salen)Tin Complexes:Syntheses,Characterization,Crystal Structures,and Catalytic Activity in the Formation of Propylene Carbonate from CO_2 and Propylene Oxide.Inorg.Chem.,2004,43(14):43 15-4327.
(d)常涛,吴梅,靳丽丽,等.溴化锌-季翁三溴盐催化二氧化碳和环氧化合物偶联反应.催化学报,2007,28(5):404-406.
(e)靳丽丽,常涛,景欢旺.钌卟啉络合物催化二氧化碳与环氧化合物偶联反应.催化学报,2007,28(4):287-289.
[5]Gembicky M,Boca R and Renz F.A Heptanuclear Fe(Ⅱ)-Fe(Ⅲ)System with Twelve Unpaired Electrons,Inorg.Chem.Commun..2000,3(11):662-665.
[6](a)邱传亮,王德心等.氨基二元酸的Boc化研究.化学试剂,2004,26(1):37-38.
(b)李美玲,许艳杰,姜丽琴等.三肽N-O-Ns-Gly-N-Me-D-Phe-L -Pro-OMe的合成.化学通报,2006年第3期,179-183.
(c)程永浩,刘守信,N-酰化脯氨酰氯合成及其机理研究,河北师范大学学报(自然科学版),2001,25(2):205-207.
(d)Hu M.X.,Li N..Synthesis and Characterization of Rare Earth Complexes with Phthalaldehyde-lysine Schiff base.Front.Chem.China.,2006,4:369-373.
[7]尹振明,杨文智,邻-二(吡咯-2-甲酰胺基)亚苯的合成、晶体结构及阴离子识别,高等学校化学学报.2004,25(7):1260-1263.
[8]Salehzadeh S,Nouri S.M,Synthesis of Gadolinium(Ⅲ)and Samarium(Ⅲ)Complexes of New Potentially Heptadentate(N_4O_3)Tripodal Schiff Base Ligands and a Theoretical Study.Polyhedron,2005,24(12):1478-1486.
[1]Melson.GA.,plenum..Coordination Chemisty of Macrocyclic Compounds [M],New York,1979.
[2]L Ehn J.M,S Mon.J.,Wagner J..Molecule Receptors 2 Molecular and Cation Complexes with Macrotricyclic and Macrotetracyclic Ligands.Angew.Chem.,1973,85(14):622.
[3]Jackel.S.G,Rose.N.J.Encapsulation Reaction,Synthesis and Characterization of Cheletes Derived from Iron(E),Diemthylglyoxime and Boron Compounds.Inorg.Chem.,1973,12(6):1232.
[4]Boston.D.R,Rose.N.J..Encapsulation Reactions,Synthesis and Study of Clathro Chelates Derived from Dimethylglyoxime,Cobalt,and Lewis Acids.J.Am.Chem.Soc,1973,95(13):4163.
[5]Goedken V L.,Peng.S.M..Template Condensations:Metal Ion Direted Syntheses of Macrocyclic,Tricyclic and Quadricyclic Metal Complexes from 2,3-butanedione Dihydrazone and Formalclehyed.J.Chem.Soc.Chem Commum., 1973, (3): 62.
[6] Koyama H., Yoshino.T.. Synthesis of Some Medium Sized Cyclic Triamine and Their Cobalt(III) Complexs. Bull. Chem. Chem. Soc. Jpn., 1972,45: 481.
[7] Rodgers S. J., Chiu Yuen Ng, Raymond K. N.. High-Dilution Synthesis of Macrocyclic Polycatecholates. J. Am. Chem. Soc, 1985,107(13): 4094-4095.
[8] (a) Thomas J. McMurry., Steven J. Rodgers., Kenneth N. Raymond.. Template and Stepwise Syntheses of a Macrobicyclic Catechoylamide Ferric Ion Sequestering Agent. J. Am. Chem. Soc. 1987, 109(11): 3451-3453.
(b) Garrett T. M., McMurry T. J., Zelideth E., Raymond K. N. Synthesis and Characterization of Macrobicyclic Iron(III) Sequestering Agents. J. Am. Chem. Soc. 1991. 113(8): 2965-2977.
(c) K arpishin T.B., Stack T.D.P., Raymond K. N.. Octahedral vs Trigonal Prismatic Geometry in a Series of Catechol Macrobicyclic Ligand-Metal Complexes. J. Am. Chem. Soc. 1993. 115: 182-192.
[10] Armands K., Wright P. J., Tsao Meng-Lin e tal.. Photoenolization of 2-(2-Methyl Benzoyl) Benzoic Acid, Methyl Ester: Effect of E Photoenol Lifetime on the Photochemistry. J. Org. Chem., 2005, 70(7): 2763-2770.
[2]李昆瑜.CO_2的应用及产品开发.天然气化工(C 化学与化工),1996,21(3):40-43.
[3]周忠清.二氧化碳催化还原成碳的发展.精细石油化工,1994,(4):92-96
[4]李淑芬,陈宝良,韩金玉.超临界CO_2萃取天然产品的特性研究.化工进展,1997,(2):10-14.
[5]谈士海,张文正.非混相CO_2驱油在油田增产中的应用.石油钻探技术,2001,29,(2):58-59.
[6]Aresta M..Perspectives of Carbon Dioxide Utilisation In the Synthesis of Chemicals Coupling Chemistry with Biotechnology.Stud.Surf.Sci.Catal.,1998,114:65-76.
[7]梁斌.CO_2与环氧丙烷不对称环加成反应催化体系的设计与研究[D].大连理工大学硕士学位论文,2004.3.
[8]Dean C.W..Cyclic Carbonate Functional Polymers and Their Applications.Progr.Org.Coat.,2003,47(1):77-86.
[9]Alicja.W.,Lech C..A Comparison of Acid-Base Properties of Substituted Pyridines and Their N-Oxides in Propylene Carbonate.J.Chem.Thermodynamics.,1998,30(6):713-722.
[10]Wei T.,Wang M.,Wei W.,Sun Y.H.,Zhong B..Effect of Base Strength and Basicity on Catalytic Behavior of Solid Bases for Synthesis of Dimethyl Carbonate from Propylene Carbonate and Methanol.Fuel.Process.Technol.,2003,83(1-3):175-182.
[11]宝中明秀.碳酸丙烯醋复合溶剂研究.化学工程,1999,27(2):51-53.
[12]Le Q.H.,Yan S.,Tu J.L..A New Complex Absorbent Used for Improving Propylene Carbonate Absorbent for Carbon Dioxide Removal.Sep.Purif.Technol.,1999,16(2):133-138.
[13]陈卫祥,杨兰生,单志强,邹建梅,刘黎.全固态锂电池用聚合物电解质的 研究.电源技术,1996.20(2):50-54.
[14]Wolfenstine.J.,Shictman M.,Read J.,Foster D.,Behl W..The Effect of the Mn-Ion Oxidation State on Propylene Carbonate Decomposition.J.Power Sources,2000,91(2):118-121.
[15]朱宏,陈立班,江英彦.均相催化剂催化合成碳酸丙烯酯.天然化工(C1化学与化工),1997,22(1):9-11.
[16]陶洪连,黄敏.碳酸丙烯酯脱碳装置技术改造小结.化学工业与工程技术,2002,23(5):27-29.
[17]Hou X.P.,Kok S.Ionic Conductivity and Electrochemical Characterization of Novel Interpenetrating Polymer Network Electrolytes.Solid State Ionics,2002,147(3-4):391-395.
[18]Behr A..Carbon Dioxide Activation by Metal Complex.New York:VCH Publishers.1988,91-93.
[19]Rokicki A.,Kuran W.,Marcinick B.P..Cyclic Carbonates from Carbon Dioxide and Oxiranes.Monatsch.Chem.,1984,115(2):205-214.
[20]江琦,黄仲涛.CO_2与环氧丙烷环加成的催化剂及反应工艺研究.天然气化工(C 化学与化工),1996,21(6):2-24
[21]Kihara N.,Hara N.,Endo T..Catalytic Activity of Various Salts in the Reaction of 2,3-Epoxypropyl Phenyl Ether and Carbon Dioxide under Atmospheric Pressure.J.Org.Chem.,1993,58(23):6198-6202.
[22]Krasimir K.,Neli K.,Kolio T..Calcium Chloride as Co-Catalyst of Onium Halides in the Cycloaddition of Carbon Dioxide to Oxiranes.J.Mol.Catal.,A:Chem.,2003,194:29-37.
[23]Nishikubo T.,Kameyama A.,Yamashita J.,Tomoi M.,Fukuda W..Insoluble Polystyrene-Bound Quaternary Onium Salt Catalysts for the Synthesis of Cyclic Carbonates by the Reaction of Oxiranes with Carbon Dioxide.J.Polym.Sci.,Part A:Polymer.Chem.,1993,31(4):939-947.
[24]Matsuda H.,Ninagawa A.,Nomura R..Reaction of Carbon Dioxide with Epoxides in the Presence of Pentavalent Organoantimony Compounds.Chem.Lett.,1979,(2):1261-1262.
[25] Nomura R., Ninagawa A., Matsuda H.. Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides in the Presence of Organoantimony Compounds as Novel Catalysts. J. Org. Chem., 1980,45(19): 3735-3738.
[26] Nomura R., Kimura M., Ninagawa A., Matsuda H.. Direct Synthesis of Cyclic Carbonates in the Presence of Organometallic Compounds. Catalyses of Systems from Group IVA, VA, and VIA Compounds and A Lewis Base. Bull. Chem. Soc. Jpn., 1982, 55(10): 3200-3203.
[27] Baba A., Nozaki T., Matsuda H.. Carbonate Formation from Oxiranes and Carbon Dioxide Catalyzed by Organotin Halide-Tetraalkylphosphonium Halide Complexes. Bull. Chem. Soc Jpn., 1987,60(4): 1552-1554.
[28] Jing H. W., Smita K. E., Julianne M. G., Charlotte L. S., Hongying Zhou.. (Salen)Tin Complexes: Syntheses, Characterization, Crystal Structures, and Catalytic Activity in the Formation of Propylene Carbonate from CO_2 and Propylene Oxide. Inorg. Chem. 2004,43(14): 4315-4327.
[29] Gupta M. K., Singh H. L., Tripaathi U. D., Varshney A. K.. Bull.Pol. Acad. Sci. Chem. 2000,48,195-201.
[30] Atwood D. A., Jegier J. A., Martin K. J., Rutherford D.. J. Organomet. Chem. 1995, 503, C4-C7.
[31] Paddock R. L., Nguyen S. T.. Chemical CO_2 Fixation: Cr(III) Salen Complexes as Highly Efficient Catalysts for the Coupling of CO_2 and Epoxides. J. Am. Chem. Soc. 2001,123(46): 11498-11499.
[32] Jing H.W., SonBinh T. Nguyen.. SnCl_4-organic Base: Highly Efficient Catalyst System for Coupling Reaction of CO_2 and Epoxides. J. Mol. Catal. A: Chem., 2007, 261(1): 12-15.
[33] Kim H. S., Kim J. J., Lee S. D., Lah M. S..New Mechanistic Insight into the Coupling Reactions of CO_2 and Epoxides in the Presence of Zinc Complexes. Chem. Eur. J. 2003, 9(3): 678-686.
[34] Allen S.D., Moore D.R., Lobkovsky E. B.. High-Activity Single- Site Catalysts for the Alternating Copolymerization of CO_2 and Propylene Oxide. J. Am.Chem. Soc, 2002,124(48): 14284-14285.
[35]Kim J.S.,Re.e.M.,Shin T.J.,Han.O.H.,Cho.S.J.,Hwang Y.-T..X-Ray Absorption and NMR Spectroscopic Investigations of Zinc Glutarates Prepared from Various Zinc Sources and Their Catalytic Activities in the Copolymerization of Carbon Dioxide and Propylene Oxide.J.Catal.,2003,218(1):209-219.
[36]Quan Z.,Wang X.H.,Zhao X.J.,Wang F S..Copolymerization of CO_2 and Propylene Oxide under Rare Earth Ternary Catalyst:Design of Ligand in Yttrium Complex.Polymer,2003,44(19):5605-5610
[37]Kisch H.,Millini R.,Wang L..Bifunktionelle Katalysatoren zur Synthese cyclischer Carbonate aus Oxiranen and Kohlendioxid.Chem.Ber.,1986,119:1090-1093.
[38]Dumlei.W,Kisch.H..Bifunktionelle Katalyse der Reaktion von Kohlendioxid mit Oxiranen.Chem.Ber,1990,123:277-283.
[39]常涛,吴梅,靳丽丽,景欢旺,邱文元.溴化锌-季鎓三溴盐催化二氧化碳和环氧化合物偶联反应.催化学报,2007,28(5):404-406.
[40]Tao Chang,Huanwang Jing,Lili Jin,Wenyuan Qiu.Quaternary Onium Tribromide Catalyzed Cyclic Carbonate Synthesis from Carbon Dioxide and Epoxides.J.Mol.Catal.A:Chem.,2007,264(1-2):241-247.
[41]Kim H.S.,Kim J.J.,Le.e.B.G.,Jung O.S.,Jang H.G.,Kang S.O..The First Isolation of Pyridinium Alkoxy Ion-bridged Dimeric Zinc Complex for the Coupling Reaction of CO_2 and Epoxides.Angew.Chem.Int.Ed.Engl.,2000,39:4096-4098.
[42]Hoon S.K,Jai K.,Honggon K.,Ho G.J.,Ho G J..Well-Defined Highly Active Heterogeneous Catalyst System for the Coupling Reactions of Carbon Dioxide and Epoxides.,J.Catal.,2002,205(1):226-229.
[43]Hoon.S.K,Jai.K.,Honggon.K.,Ho.G..J..Imidazolium Zinc TetrahalideCatalyzed Coupling Reaction of CO_2 and Ethylene Oxide or Propylene Oxide.J.Catal.,2003,220(1):44-46.
[44]Ralph J.D.P..Unusual Catalysis With Nickel(0)Complexes.J.C.S.,Chem.Comm.,1973,(5):157-158.
[45]Jan E.B.,Ola K.Stig O.L..Stereochemistry of Copper- and NickelCatalyzed Insertion of Carbon Dioxide into Epoxides.A Microwave Study.Tetrahedron Lett.,1980,21(51):4985-4988.
[46]Fujinami T.,Suzuki T.,Kamiya M.,Fuzawa S.,Sakai S..Palladium Catalyzed Reaction of Butadiene Monoxide with Carbon Dioxide.Chem.Lett.,1985,(2):199-200.
[47]Trost B.M.,Angle A.R..Palladium-Mediated Vicinal Cleavage of Ally1Epoxides With Retention of Stereochemistry:A Cis Hydroxylation Equivalent.J.Am.Chem.Soc.,1985,107(21):6123-6124.
[48]Hiroyuki Y.,H.L.-N.,Toshiyasu S..Cyclic Carbonate Synthesis from Supercritical Carbon Dioxide and Epoxide over Lanthanide Oxychloride.J.Catal.,2002,209:547-550.
[49]Lili Jin,Huanwang Jing,Tao Chang,Xiuli Bu,Li Wang,Zhongli Liu..Metal Porphyrin/Phenyltrimethylammonium Tribromide:High Efficient Catalysts for Coupling Reaction of CO_2 and Epoxides.J.Mol.Catal.A:Chem.,2007,261(2):262-266.
[50]靳丽丽,常涛,景欢旺.钌卟啉络合物催化二氧化碳与环氧化合物偶联反应.催化学报,2007,28(4):287-289.
[51]Michael R.,Fabian J.,Grunwaldt J.D.,Alfons B..Solventless synthesis of propylene carbonate eatalysed by chromium-salen complexes:Bridging homogeneous and heterogeneous catalysis.J.Mol.Catal.A:Chem.,2005,242(1-2):32-39.
[52]Miao C.X.,Wang J.Q.,Wu Y.,Du Y.,He L.N..Bifunctional Metal-Salen Complexes as Efficient Catalysts for the Fixation of CO_2 with Epoxides under Solvent-Free Conditions.ChemSusChem,2008,1,236-241.
[53]Michele A,Angela D.,Libero G.,Carlo P..Nb(V)Compounds as Epoxides Carboxylation Catalysts:the Role of the Solvent.J.Mol.Catal.A:Chem.,2003,204-205:245-252.
[54]Hiroyuki Y.,H.L.-N,Toshiyasu S..Cyclic Carbonate Synthesis from Supercritical Carbon Dioxide and Epoxide over Lanthanide oxychloride.J. Catal.,2002,209(2):547-550.
[55]Welton T..Room-Temperature Ionic Liquids.Solvents for Synthesis and Catalysis.Chem.Rev.1999,99(8):2071-2084.
[56]Zhao D.,Wu M..Kou Y,Min E..Ionic liquids:applications in catalysis.Catal.Today.,2002,74(1-2):157-189.
[57]彭家建,邓友全.室温离子液体催化合成碳酸丙烯酯.催化学报,2001,22(6):598-600.
[58]Hajime A.,Akiyoshi A.,Keitaro A.,Yutaka K..A Rapid and Effective Synthesis of Propylene Carbonate Using a Supercritical CO_2 Onic Liquid System.Chem.Commun.,2003,(7):896-897.
[59]Qi C.R.,Jiang H.F.,Wang Z.Y.,Zou B.,Yang S.R..Naturally Occurringamino Acid-catalyzed Coupling of Carbon Dioxide with Epoxides to Afford Cyclic Carbonates.Synlett.,2007,(2):255-258.
[60]Alessandro B.,Raimondo M.,Alessandro M.,Giovanni M.,Giovanni S.,Raffaella S..Cycloaddition of CO_2 to Epoxides over Both Homogeneous and Silica-supported Guanidine Catalysts.Tetrahedron Lett.,2003,44(14):2931-2934.
[61]Takashi Y.,Hideo M.,Takahiro K.,Hiroyasu L.,Hisashi F.,Masakuni Y.Toshihisa M..Magnesium Oxide-catalysed Reaction Of Carbon Dioxide with an Epoxide Withretention Of Stereochemistry.Chem.Commun.,1997,(12):1129-1130.
[62]Yamaguchi K.,Ebitani K.,Yoshida T.,Yoshida H.,Kaneda K..Mg-A1 Mixed Oxides as Highly Active Acid-Base Catalysts for Cycloaddition of Carbon Dioxide to Epoxides.J.Am.Chem.Soc.,1999,121(18):4526-4527.
[63]Sorana L.,Katherine W.,Mandelin P.,Benny A.,Rick W..Geometric Requirements for the Photolysis of Aryloxiranes and Cyclic Carbonate.Tetrahedron Lett.,2002,43(7):1169-1170.
[64]Hiroyuki U.,Motomu K.Masakatsu S..Studies toward the Total Synthesis of Garsubellin A:Synthesis of 8-depreny1-garsubellin A.Tetrahedron Lett.,2002,43(20):3621-3624.
[65] Jegham S., Nedelec A., Bumier P., Guminski Y., Puech F., Koenig J.J., George P.. Use of Chiral Glycerol 2,3-Carbonate in the Synthesis of 3-Aryl-2-oxazolidinones. Tetrahedron Lett., 1998, 39(25): 4453-4454.
[66] Kolb H.C., VanNieuwenhze M.S., Sharpless K.B.. Catalytic Asymmetric Dihydroxylation. Chem. Rev., 1994, 94(8): 2483-2547.
[67] Scott E. S., Bridget D. B., Jay F. L., Makoto T., Karl B. H., Alexandra E.G.. Highly Selective Hydrolytic Kinetic Resolution of TerminalEpoxides Catalyzed by Chiral (salen)Co(III) Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2- Diols. J. Am. Chem. Soc, 2002, 124(7): 1307-1315.
[68] Patrick B. Michael L. P. The Resolution of Racemic 1,2-diols By the Esterase Catalysed Hydrolysis of The Corresponding Cyclic Carbonate. Tetrahedron, 1992,48(36): 7731-7734.
[69] Srinivasan K, Michaud P, Kochi J. K.. Epoxidation of Olefins with Cationic (salen)manganese(III) Complexes. The Modulation of Catalytic Activity by Substituents. J. Am. Chem. Soc,1986,108(9): 2309- 2320.
[70] Katsuki T. Mn-salen Catalyst, Competitor of Enzymes, for Asymmetric Epoxidation. J. Mol. Cat. A, 1996,113(1-2): 87-107.
[71] Fukuda T., Katsuki T.. Highly Enantioselective Cyclopropanation of Styrene Derivatives Using Co(III)-Salen Complex as a Catalyst. Tetrahedron, 1997, 53(21): 7201-7208.
[72] Tokunaga M , L arrow J F, Jacobsen E N. Asymmetric Catalysis with Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis. Science,1997,277: 936-938.
[73] Masutani K, Uchida T, Irie R, Katsuki T. Catalytic Asymmetric and Chemoselective AerobicOxidation: Kinetic Resolution of Sec-alcohols. Tetrahedron. Lett, 2000,41(26): 5119-5123.
[74] Lu X. B., Liang B., Zhang Y. J., e tal. Asymmetric Catalysis with CO_2: Direct Synthesis of Optically Active Propylene Carbonate from Racemic Epoxides. J. Am. Chem. Soc, 2004,126(12): 3732-3733.
[75]Paddock R.T.,Nguyen S.T.,Chiral(salen)Co~Ⅲ catalyst for the synthesis of cyclic carbonates.Chem.Commun.,2004,1622-1623.
[76]Berkessel,A.,Brandenburg,M..Catalytic Asymmetric Addition of Carbon Dioxide to Propylene Oxide with Unprecedented Enantioselectivity.Org.Lett.2006,8(20):4401-4404.
[77]S.W.Chen,Kawtherkar R.B.,G J.Kim..One-pot combination of the Wittig olefination with oxidation,hydrogenation,bromination,and photocyclization reactions.Tetrahedron Lett.,2007,48(2):293.
[78]H.Tanaka.,Y.Kitaich.i,M.Sato.,T.Ikeno,T.Yamada..Enantioselective CO_2Fixation Catalyzed by Optically Active Cobalt Complexes.Chem.Lett.2004,33(6):676.
[79]W.Yamada.,Y.Kitaichi,H.Tanaka,T.Kojima,M.Sato,T.Ikeno,T.Yamada..Enantioselective Incorporation of Carbon Dioxide into Epoxides Catalyzed by Optically Active Cobalt(Ⅱ)Complexes.Bull.Chem.Soc.Jpn.2007,80(7):1391.
[80]卢毅.稀土schiff碱配合物的合成及催化环酯开环聚合[D],浙江大学硕士学位论文,2007.5.
[81]Yang Haijian,Sun Wenhan,Li Zilong,Ma Zhi.The Rapid Synthesis of /Schiff- Base without Solvent under Microwave Irradiation.Chin.Chem.Lett.,2002,13(1):3-6.
[82]Bernhardt P.V.,Bernadine M.F.,Mark J.R..Isomorphous Lanthanide Complexes of a Tripodal N_4O_3 Ligand.Aust.J.Chem.,2000,53,229-231.
[83]Bernhardt P.V.,Flanagan.B.M.,Riley.M.J..Completion of the Isomorphous Ln(trensal)Series.Aust.J.Chem.2001,54,229-232.
[84]Michael W.E.,D.Webster Keogh.,Brian L.Scott,John G.Watki..Synthesis and Structural Characterization of the Lanthanide Schiff-Base Complexes {N[CH_2CH_2N=CH(2-O-3,5-t-Bu_2C_6,H_2)]3} Ln(Ln=Sm,Nd),Polyhedron,2001,20(5):373-377.
[85]马红竹,手性镧系配合物的合成、表征及不对称催化性质研究[D].西北大 学博士学位论文,2005.3.
[86]Carmona D.,Lamata M.P.,Oro L.A..Recent Advances In Homogeneous Enantioselective Dieis-Alder Reactions Catalyzed by Chiral TransitionMetal Complexes.,Coord Chem.Chem.,2000,200-202,717-772.
[87]Shinya K.,Hirofumi Nakano,Masaaki K.,Naomichi B.,Kiyohiko N..An effect of the ionic radii of lanthanide(Ⅲ)ions on the structure andcatalytic properties of chiral Schiff base-lanthanide(Ⅲ)complexes.Inorganica.Chimica.Acta.,2003,349(5):6-16.
[88]张伟国等.氨基酸生产技术及其应用[M].中国轻工业出版社,北京:1997
[89]LI JingWei,XU LiWen,XIA ChunGu.Advances in Proline-Catalyzed Asymmetric Reactions.Chin.J.Org.Chem.,2004,24(1):23-28.
[90]Huang J.L.,Liu X.H.,Wen Y.H.,Bo Qin,Feng X.M..Enantioselective Strecker Reaction of Phosphinoyl Ketoimines Catalyzed by in Situ Prepared Chiral N,N-Dioxides.J.Org.Chem.,2007,72(1):204-208.
[91]李宁,姚克敏,楼开炎等,La(Ⅲ),Y(Ⅲ)与多甘醇醛缩氨基酸Schiff碱配合物的合成及其固体高分辨-(13)CNMR波谱.中国科学,B辑,1999,29(5):450-455.
[1](a)Mizukami S,Houjou H,Kanesato M,et al.Adjustment of Twist Angles in Pseudo-Helical Lanthanide Complexes by the Size of Metal Ions.Chem.Eur.J.2003,9(7):1521-1528.
(b)Essig M.W,Keogh D.W,Scott B.L,et al.Synthesis and structural characterization of the lanthanide Schiff-base complexes {N[CH_2CH_2N=CH(2-O-3,5-tert-BuC_6H_2)]3}Ln(La,Sm,Nd)[J].Polyhedron,2001,20(5):373-377.
[2](a)Kano S.,Nakano H..An Effect of The Ionic Radii of Lanthanide(Ⅲ)Ions on the Structure and Catalytic Properties of Chiral Schiff Base-Lanthanide(Ⅲ)Complexes.Inorganica Chimica.,Acta,2003,349(5):6-16.
(b)Carmona D,Lamata M.P.,Oro L.A..Recent Advances In Homogeneous Enantioselective Diels-Aider Reactions Catalyzed by Chiral Transition-Metal Complexes,Coord.Chem.Rev.,2000,200-202,717-772.
[3](a)Han Zhi-jian,Wang Rui,Zhou Yi-feng,et al.Simple Derivatives of Natural Amino Acids as Chiral Ligands in the Catalytic Asymmetric Addition of Phenylacetylene to Aldehydes,Eur.J.Org.Chem.,2005,2005(5):934-938.
(b)Traverse J.F.,Yu Zhao,Hoveyda A.H.,et al,Proline-Based N-Oxides as Readily Available and Modular Chiral Catalysts.Enantioselective Reactions of Allyltrichlorosilane with Aldehydes.Org.Let.,2005,7(15):3151-3154.
(c)魏丹毅,李冬成,姚可敏等.稀土元素与丙氨酸SChiff碱双核配合物的合成与表征及催化活性.无机化学学报,1998,14(2):209-214.
[4](a)Chang Tao,Jing Huanwang,Jin Lili et al.Quaternary Oninm Tribromide Catalyzed Cyclic Carbonate Synthesis from Carbon Dioxide and Epoxides.J.Mol.Catal.A:Chem.,2007,264(1-2):241-247.
(b)Jin L.I.,Jing H.W.,Chang T.et al..Metal Porphyrin/phenyltrimethyltribromide:High Efficient Catalysts for Coupling Reaction of CO_2 and Epoxides.J.Mol.Catal.A:Chem.,2007,261(1-2):262-266.
(c)Jing H.W.,Edulji S.K.,Nguyen S.T.et al.(Salen)Tin Complexes:Syntheses,Characterization,Crystal Structures,and Catalytic Activity in the Formation of Propylene Carbonate from CO_2 and Propylene Oxide.Inorg.Chem.,2004,43(14):43 15-4327.
(d)常涛,吴梅,靳丽丽,等.溴化锌-季翁三溴盐催化二氧化碳和环氧化合物偶联反应.催化学报,2007,28(5):404-406.
(e)靳丽丽,常涛,景欢旺.钌卟啉络合物催化二氧化碳与环氧化合物偶联反应.催化学报,2007,28(4):287-289.
[5]Gembicky M,Boca R and Renz F.A Heptanuclear Fe(Ⅱ)-Fe(Ⅲ)System with Twelve Unpaired Electrons,Inorg.Chem.Commun..2000,3(11):662-665.
[6](a)邱传亮,王德心等.氨基二元酸的Boc化研究.化学试剂,2004,26(1):37-38.
(b)李美玲,许艳杰,姜丽琴等.三肽N-O-Ns-Gly-N-Me-D-Phe-L -Pro-OMe的合成.化学通报,2006年第3期,179-183.
(c)程永浩,刘守信,N-酰化脯氨酰氯合成及其机理研究,河北师范大学学报(自然科学版),2001,25(2):205-207.
(d)Hu M.X.,Li N..Synthesis and Characterization of Rare Earth Complexes with Phthalaldehyde-lysine Schiff base.Front.Chem.China.,2006,4:369-373.
[7]尹振明,杨文智,邻-二(吡咯-2-甲酰胺基)亚苯的合成、晶体结构及阴离子识别,高等学校化学学报.2004,25(7):1260-1263.
[8]Salehzadeh S,Nouri S.M,Synthesis of Gadolinium(Ⅲ)and Samarium(Ⅲ)Complexes of New Potentially Heptadentate(N_4O_3)Tripodal Schiff Base Ligands and a Theoretical Study.Polyhedron,2005,24(12):1478-1486.
[1]Melson.GA.,plenum..Coordination Chemisty of Macrocyclic Compounds [M],New York,1979.
[2]L Ehn J.M,S Mon.J.,Wagner J..Molecule Receptors 2 Molecular and Cation Complexes with Macrotricyclic and Macrotetracyclic Ligands.Angew.Chem.,1973,85(14):622.
[3]Jackel.S.G,Rose.N.J.Encapsulation Reaction,Synthesis and Characterization of Cheletes Derived from Iron(E),Diemthylglyoxime and Boron Compounds.Inorg.Chem.,1973,12(6):1232.
[4]Boston.D.R,Rose.N.J..Encapsulation Reactions,Synthesis and Study of Clathro Chelates Derived from Dimethylglyoxime,Cobalt,and Lewis Acids.J.Am.Chem.Soc,1973,95(13):4163.
[5]Goedken V L.,Peng.S.M..Template Condensations:Metal Ion Direted Syntheses of Macrocyclic,Tricyclic and Quadricyclic Metal Complexes from 2,3-butanedione Dihydrazone and Formalclehyed.J.Chem.Soc.Chem Commum., 1973, (3): 62.
[6] Koyama H., Yoshino.T.. Synthesis of Some Medium Sized Cyclic Triamine and Their Cobalt(III) Complexs. Bull. Chem. Chem. Soc. Jpn., 1972,45: 481.
[7] Rodgers S. J., Chiu Yuen Ng, Raymond K. N.. High-Dilution Synthesis of Macrocyclic Polycatecholates. J. Am. Chem. Soc, 1985,107(13): 4094-4095.
[8] (a) Thomas J. McMurry., Steven J. Rodgers., Kenneth N. Raymond.. Template and Stepwise Syntheses of a Macrobicyclic Catechoylamide Ferric Ion Sequestering Agent. J. Am. Chem. Soc. 1987, 109(11): 3451-3453.
(b) Garrett T. M., McMurry T. J., Zelideth E., Raymond K. N. Synthesis and Characterization of Macrobicyclic Iron(III) Sequestering Agents. J. Am. Chem. Soc. 1991. 113(8): 2965-2977.
(c) K arpishin T.B., Stack T.D.P., Raymond K. N.. Octahedral vs Trigonal Prismatic Geometry in a Series of Catechol Macrobicyclic Ligand-Metal Complexes. J. Am. Chem. Soc. 1993. 115: 182-192.
[10] Armands K., Wright P. J., Tsao Meng-Lin e tal.. Photoenolization of 2-(2-Methyl Benzoyl) Benzoic Acid, Methyl Ester: Effect of E Photoenol Lifetime on the Photochemistry. J. Org. Chem., 2005, 70(7): 2763-2770.