手性联二萘衍生物的合成、固载化以及催化氢化的研究
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摘要
不对称催化是有机化学的前沿领域和发展方向。近年来,寻找高对映选择性和高催化活性的手性配体,通过对均相催化剂负载解决昂贵的手性金属催化剂的分离和回收实现面向绿色化和实用化的不对称催化是最近不对称催化研究热点问题。本论文利用具有C2轴手性的联二萘酚为原料合成了一系列3位和3,3'位取代的手性联二萘酚衍生物,并将其应用于四烯丙基锡对苯甲醛的烯丙基化催化反应,获得了较好的催化效果。同时;利用具有可控的介孔纳米无机材料SBA-15作载体,将手性联二萘酚单磷配体通过与金属钌进行配位,同时进行固载化,实现了均相催化剂负载。探讨了此类具有介孔结构的负载型催化剂在芳香酮的催化加氢化反应的催化性能。主要研究如下:
一,3位和3,3'位取代的手性联二萘酚衍生物的合成及其在苯甲醛的烯丙基化加成反应中的应用。从手性联二萘酚出发,经过多步反应制备了一系列3,3'位取代的手性联二萘酚衍生物;探讨了在四烯丙基锡对苯甲醛烯丙基化的加成反应中应用,研究结果发现:除3c转化率为73.2%,其余转化率都大于90%,3b更是>99%,同不用催化剂比较,其转化率大大提高,同BINOL比较,3b,3c也具有更明显的效果。
二,介孔材料SBA-15负载的手性联二萘酚类单磷配体金属催化剂的合成及在芳香酮的不对称催化加氢化反应中的应用。从手性联二萘酚出发,经过多步反应制备了具有介孔结构的SBA-15负载的手性金属钌催化剂。考察了取代芳香酮的不对称催化氢化,这种负载型金属催化剂在芳香酮的不对称催化氢化展示了高的催化反应活性。
Asymmetric Catalysis is the forefront of the field of organic chemistry and the direction of development. In recent years, the search for high enantioselectivity and high catalytic activity of chiral ligands, by homogeneous catalyst load solution of the hands of expensive metal catalyst separation and recycling of green-oriented and practical use of the asymmetric catalysis is the latest Asymmetric Catalysis on hot issues. In this paper, using a C2-hand of Binaphthol synthesized a series of three and 3,3 '-substituted chiral Binaphthol derivatives, and applied to four allyltin p Formaldehyde Allylation of catalytic reaction was better catalytic effect. At the same time the use of a controllable mesoporous Nanoinorganics SBA-15 for the carrier, will hand of the two single-naphthol phosphorus ligand with a metal ruthenium coordination, supported at the same time, achieve a homogeneous catalyst load. Discussion of such a mesoporous structure of supported catalysts in the hydrogenation of aromatic ketones catalytic properties of the catalytic reaction. Major research are as follows:
First,1,3 and 3,3 '-substituted chiral Binaphthol derivatives of benzene and formaldehyde in the reaction of allyl the application. From the hands of Binaphthol departure, after multi-step reaction of a series of 3,3 '-substituted chiral Binaphthol derivatives; discussed in the four allyltin allyl of benzaldehyde Reaction in the application of results of the study found that: In addition to three c conversion rate is 73.2% and the remaining conversion rate of more than 90%, 3 b is> 99%, compared with no catalyst, the conversion rate greatly improved, compared with BINOL, 3 b , 3c also has a more pronounced effect.
Second, mesoporous materials SBA-15 load of the hands of the two phenolic naphthalene single phosphorus ligand and metal catalysts in the synthesis of aromatic ketones asymmetric hydrogenation reaction in the application. From the hands of Binaphthol departure, after a multi-step reaction of a mesoporous structure of the SBA-15 load chiral ruthenium metal catalyst. Replace aromatic ketones inspected the asymmetric hydrogenation, which supported metal catalysts aromatic ketones in the asymmetric hydrogenation catalysts demonstrated high catalytic activity.
一,3位和3,3'位取代的手性联二萘酚衍生物的合成及其在苯甲醛的烯丙基化加成反应中的应用。从手性联二萘酚出发,经过多步反应制备了一系列3,3'位取代的手性联二萘酚衍生物;探讨了在四烯丙基锡对苯甲醛烯丙基化的加成反应中应用,研究结果发现:除3c转化率为73.2%,其余转化率都大于90%,3b更是>99%,同不用催化剂比较,其转化率大大提高,同BINOL比较,3b,3c也具有更明显的效果。
二,介孔材料SBA-15负载的手性联二萘酚类单磷配体金属催化剂的合成及在芳香酮的不对称催化加氢化反应中的应用。从手性联二萘酚出发,经过多步反应制备了具有介孔结构的SBA-15负载的手性金属钌催化剂。考察了取代芳香酮的不对称催化氢化,这种负载型金属催化剂在芳香酮的不对称催化氢化展示了高的催化反应活性。
Asymmetric Catalysis is the forefront of the field of organic chemistry and the direction of development. In recent years, the search for high enantioselectivity and high catalytic activity of chiral ligands, by homogeneous catalyst load solution of the hands of expensive metal catalyst separation and recycling of green-oriented and practical use of the asymmetric catalysis is the latest Asymmetric Catalysis on hot issues. In this paper, using a C2-hand of Binaphthol synthesized a series of three and 3,3 '-substituted chiral Binaphthol derivatives, and applied to four allyltin p Formaldehyde Allylation of catalytic reaction was better catalytic effect. At the same time the use of a controllable mesoporous Nanoinorganics SBA-15 for the carrier, will hand of the two single-naphthol phosphorus ligand with a metal ruthenium coordination, supported at the same time, achieve a homogeneous catalyst load. Discussion of such a mesoporous structure of supported catalysts in the hydrogenation of aromatic ketones catalytic properties of the catalytic reaction. Major research are as follows:
First,1,3 and 3,3 '-substituted chiral Binaphthol derivatives of benzene and formaldehyde in the reaction of allyl the application. From the hands of Binaphthol departure, after multi-step reaction of a series of 3,3 '-substituted chiral Binaphthol derivatives; discussed in the four allyltin allyl of benzaldehyde Reaction in the application of results of the study found that: In addition to three c conversion rate is 73.2% and the remaining conversion rate of more than 90%, 3 b is> 99%, compared with no catalyst, the conversion rate greatly improved, compared with BINOL, 3 b , 3c also has a more pronounced effect.
Second, mesoporous materials SBA-15 load of the hands of the two phenolic naphthalene single phosphorus ligand and metal catalysts in the synthesis of aromatic ketones asymmetric hydrogenation reaction in the application. From the hands of Binaphthol departure, after a multi-step reaction of a mesoporous structure of the SBA-15 load chiral ruthenium metal catalyst. Replace aromatic ketones inspected the asymmetric hydrogenation, which supported metal catalysts aromatic ketones in the asymmetric hydrogenation catalysts demonstrated high catalytic activity.
引文
1. Brunner, H. and Zettlmeier W.; Eds. Handbook of Enantioselective Catalysis; VCH; New York, 1993; Vol.2.
2. Noyori, R. J. Am. Chem. Soc. 1987, 109, 5856.
3. Jacobsen, E. N. Tetrahedron. 1994, 50, 4323.
4. Pritchett, S.; Woodmansee, D. H.; Davis, T. J.; Waksh, P. J. Tetrahedron Lett. 1998, 39, 5941.
5. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
6.Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem. Chem. Int. Engl. 1997, 36, 1871.
7. Mikami,K.;Terada,M.;Nakai,T., Chem.Express, 1989, 4, 589
8. Noyori,R.;Tomino,l.;Tanimoto,Y ., J.Am.Chem.Soc., 1979, 101, 3129.
9. (a) Kagan,H .B .;Riant,O., Chem.Rev., 1992, 92 ,1007. (b) Mikami,K .;Shimizu,M ., Chem .Rev., 1992, 92, 1021. (c) Noyori,R.Asymmetric Catalysisin Organic Synthesis;Wiley and Sons: New York, 1994.
10.(a) Artz, S. P.; DeGrandpre, M. P.; Cram, D. J., J. Org. Chem., 1985, 50, 1486. (b) Ohki,A.;Miyashita,R .;Naka,K .;Maeda,S. ,Bull. Chem.Soc.Jpn, 1991, 64 ,2714
11. Maruoka,K .;Itoh,T.;Shirasaka,T.;Yamamoto,H ., J. Am.Chem.Soc, 1998, 110, 310.
12. (a) Hawkins, J. M.; Loren, S.; Nambu, M., J. Am. Chem. Soc., 1994, 116, 1657. (b) Aggarwal,V .K .;Anderson,E .;Giles,R .;Zaparucha,A ., Tetrahedron:Asymmetry 1995, 6, 1301. (c) Ishihara,K .;Yamamoto,H .,J. Am.Chem.Soc, 1994, 116, 1561.
13. (a) Ishihara, K.; Kurihara, H.; Yamamoto, H., J. Am. Chem. Soc., 1996, 118, 3049 (b) Ish ih ara,K.; Kurihara, H.; Matosumoto, M.; Yamamoto, H., J.Am, Chem. Soc, 1998, 120 , 6920. (c) Ishihara, K .;Kondo,S.; Kuirhara,H.; Matosumoto, M.; Yamamoto, H., J. Org. Chem., 1997, 62, 3026. (d) Yamamoto,H .;Yanagisawa,A ;Ishihara,K ;Saito,S ., Pure Appl.Chem., 1998, 70 ,1507.
14.Sasai, H .; Tokunaga, T .; Watanabe, S .; Suzuki, T ; Itoh, N; Shibasaki, M., J. Org. Chem. 1995 , 60, 7388
15. For dierct catalytic asymmetirca aldol reaction see:Yoshikawa,N.; Yamada,Y. M. A; Das, J.; Sasai, H .;Shibasaki,M .,J.Am.Chem.Soc.,1999,121,4168
16. Ding,K .L .;Ishii,A .;Mikami,K .,Angew.Chem.,Int.Ed .,1999,20 ,65 .
17.Mikami,K .;Ding,K .L.;Ishii,A .;Tanaka,A .;Sawada}N .;Kudo,K .,Chromatography,1999 ,20,65.
18.(a)Shibasaki,M .;Sasai,H .;Ara,T.,Angew.Chem.,Int.Ed.,1997,36,1236. (b)Shibasai,M.;Sasai,H.;Arai,T .;Iida,T .,Puer.Appl.Chem.,1998,70,1027. (c)Shibasaki,M .;Gorger, H .T .,Organomet.Chem.,1999,2, 199.
19.Yamada,K .;Harwood,S.J. ;Gorger,H ;Shibasaki,M .,Angew.Chem., Int. Ed., 1999, 38, 3504.
20.Nemoto,T .;Ohshima,T .;Yamaguchi,K .;Shibasaki,M .,J.Am.Chem.Soc.,2001,1233725 .
21.(a)Gao,G .;Moore,D .;Xie,R .-G.;Pu ,L. ,Org.Lett.,2002,4(23),4143.4146. (b)Moore,D.; Pu ,L .,Org.Lett.,2002,4(11),1855-1857.
22.Gao,G .;Xie,R- -G.;Pu ,L. ,PN AS,20 04,10 1(15),5417-5420.
23.S.Hashiguch,A.Fujii,J.Takehara,et.al,, J.Am.Chem.Soc., 117,7562(1995 )
24. T.Langer,G.Helmchen,Tetrahedron Letters,37,1987 (1996).
25. (a)J.X.Gao,T.Ikariya,R.Noyori,Organometallics,15,1087(1996);
26 .C.Botteghi,et.al,J.Organomet.Chem.304 ,217(1986)
27. S.Yamaguchi,et.al.,Tetrahedron:Asymmetry,4,143(1993)
28. G.Zassinovich,et.al.,J.Mol.Catal.,42,81(1987).
29. G.Zassinovich,et.al.,J.Organomet.Chem.,370,187(1989)
30. G.Mestroni,et.al., J.Mol.Catal.,l18,33(1983)
31. Guohua Liu, Mei Yao, Fang Zhang, Yan Gao and Hexing Li.,Chem. Commun., 2007, 1–4
32. Nathaniel,J.;Alcick.Tetrahydron Asymmetion 2002,13,2485-2490.
33. Ekkehard.Lindner.,Inorganic.Chemica.Acta.2003,350,49-56.
34. S.Fiorilli,B.Onida,B.Bonelli,E.Garrone,j.Phys.Chem.B,2005,109:16725-16729.
35. GM.Schwab, FRost,L. Rudolph , Kolloold-Zeitschrif 1934 , 68 , 157
36. D.Lipkin,TD.Stewart,J.Am.Chem .Soc.,1939,61,3297
37. W A .Herrmann.,C.W Kohlpaintner, Angew.Chem.Int.Ed.Eng,1993,32,1524
38. R.Selke, M.Capka, J.Mol.Catal.1990, 63, 319.
39. A.Vaccari.,Catal.Today.,1998,41,53.
40.李晓红,李灿,化学进展,2003 , 15, 204.
41.(a)K.T.Wan,M.E.Davis,J.Catal,1995,152,25.,(b)K.T.Wan,M.E.Davis,Nature.1994 ,370
42.马红霞,四川大学博士论文.2003 ,
43.Ohkuma, H Takeno,Y Honda , R Noyori-Adv.Synth.Catal .2001,343,369
44.(a)S.Itsuno,M.Takahashi,A.Tsuji,MacromL.Symp.,2004,217,191.; (b)S.ItsA.Tsuji,M.Takahashi,J.Polymer.Science.,2004,42,4556.; (c)S.Itsuno,M.Takahash.Tsuji,Tetrahedron .Lett.2003,44,3825.
45. A.Hu,H.L.Ngo,WB. Liu, J.Am.Chem.Soc.2003,125,11490.
46. P.Liu,P.Gu, F.Wang, YQ.Tu, Org.Letters,2004,6,169
47 Bayston,D.J.;Travers,C.B.;Pobnvka,M.E.C.Tetrahedron:Asymmetry 1998,9,2015.
48 Adima,A.;Moreau ,J.J.E. ;Chi Man,M.W.Chirality.2000,12,411.
49 B. F. G.Johnson, S. A. Raynor, D. S. Shephard, T. Mashmeyer, J. M. Thomas, G. Sankar, S. BromLey, R. Oldroyd, L. Gladden, M. D. Mantle,“Superiorperformance of a chiral catalyst confined within mesoporous silica”, Chem. Commun., 1999, 1167.
50 P.N.Liu,J.G.Deng,Y.Q.Tu,S.H.Wang,“Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in water”, Chem.Commun., 2004, 2070.
51 P.N.Liu,P.M.Gu,F.Wang,Y.Q.Tu,“Efficient heterogeneous asymmetric transfer hydrogenation of ketones using highly recyclable and accessible silica-immobilized Ru-TsDPEN catalysts”,Org.Lett., 2004, 6:169
52 Sanchez C,Ribot F,Organic/inorganic hybrid materials,NewJ.Chem., 1994, 18(22)1007-1047.
53.Luan, Z.;Cheng, C.F.; Zhou,W; Klinoski, J.J.Phys.Chem .1995.99, 1018.
54 .Fu, G.;Fyfe, C.A.;Schwieger, W .Kokotaill, G. Angew. Chem.,Int.Ed.Eng. 1995, 34, 1499.
55.Fyfe,C.A;Fu,G..J.Am.Chem.Soc.1995, 117, 9709.
56 Takeguchi,T.;Kim,J.B.;Kang,M.;Inui,T.;Cheuh,W.T.;haller,G.L.J.Catat. 1998, 175
57 Sayari,A.;Danumah,C.;Moudarkoski,I.L.Chem.Mater 1995, 7,813
58 Zhang,M.;Fr?b,M.;Wang,J.Tanev,P.T.;Wong,J.; J.Am.Chem.Soc.1996,118,9164
59 Blasco,T,; Corma,A;Navarro,M.T.;Pariete,J. P.J .Catal. 1995 , 156, 65
60 Alba,M.A .;Luan,Z;Klinowski, J.J.Phys.Chem.1996, 100, 2178.
61Wei,D.;wang,H.;Feng,X.;Chueb,W.-T.;Ravikovitch,P.;Lyubovsky,M.;Li,C;takeduchi,T.;haller,G.L.J.Phys.Chem.B.1998,103,2113.
62 Chatterjee,M.;Iwasaki,T.;Hayashi,H.;Onodera,Y;Ebina,; Chem.Mater.1999, 11, 1368.
63 Zhao,D.;Goldfarb,D.J.Chem.Soc.Chem.Commun.1995,875,
64 a) Tuan, B. Z.; Tu, B.; Zhao, D. Y. Nature Materials, 2003, 2, 159. b) Xiao, F. S. J. Am. Chem. Soc., 2002, 122, 888.
65 Zheng, S.; Gao, L.; Guo, J. Mater. Chem. Phys., 2001, 71, 174.
66 De Vos, D. E.; Dams, M.; Sels, B. F.; Jacobs, P. A. Chem. Rev. 2002, 102, 3615.
67 Raynor, S. A.; Thomas, J. M.; Raja, R.; Johnson, B. F. G.; Bell, R. G.; Mantle, M. D. Chem. Commun. 2000, 1925.
68 de Rege, F. M.; Morita, D. K.; Ott, K. C.; Tumas, W.; Broene, R. D. Chem. Commun. 2000, 1797.
69 a) B. F. G. Johnson, S. A. Raynor, D. S. Shepard, T. Mashmeyer, J. M. Thomas, G. Sankar, S. BromLey, R. Oldroyd, L. Gladden, M. D. Mantle, Chem. Commun. 1999, 1167; b) B. Pugin, H. Landert, F. Spindler, H. U. Blaser, Adv. Synth. Catal. 2002, 344, 974; d) M. J. Alcón, A. Corma, M. Iglesias, F. SZnchez, J. Organomet. Chem. 2002, 655, 134. c) P. N. Liu, P. M. Gu, F.Wang, Y. Q. Tu, Org. Lett. 2004, 6, 169; b] P.-N. Liu, P.-M. Gu, J.-G. Deng, Y.-Q. Tu, Y.-P. Ma, Eur. J. Org. Chem. 2005, 3221. d) P. N. Liu, J. G. Deng, Y. Q. Tu, S. H. Wang, Chem. Commun. 2004, 2070.
70a) Jiang, D. M.; Yang, Q. H., Yang, J.; Zhang, L.; Zhu, G. R.; Su, W. G.; Li, C. Chem. Mater. 2005, 17, 6154-6160. b) Jiang, D. M.; Gao, J. S.; Qihua Yang, Q. H.; Yang, J.; Li, C. L. Chem. Mater. 2006, 18, 6012-6018.
71 Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369.
72 Knowles, W. S.; Sabacky, M. J. U. S. Patent 3849480, 4005127, 4142992, 4220590.
73 Knowles, W. S. J. Chem. Educ. 1968, 63, 222. 67.
74 Chan, A. S. C. CHEMYTECH. 1993, 23, 46.
[1] 孙健,胡文浩,具有C:对称轴的手性配体及其不对称催化反应,合成化学,1995,3(1):1 9-28.
[2] Pu L. 1,1'-binaphthyl dimers, oligomers, and polymers:molecular recognition, asymmetric cat aly sis ,an dn ewm aterials[J].Chem.Rev.,1998,98:2405-2494.
[3] 郭红超,王敏。联蔡衍生物作为手性配体在不对称氢化中的应用,2000,20 ( 4 ):486-498
[4] Fan, Q. -H.; Deng, G. -J.; Lin, C. -C.; Chan, A. S. C. Tetrahedron: Asymmetry . 2001, 12, 1241.
[5] (a) Fan, Q. -H.; Ren, C. -Y.; Yeung, C. -H.; Hu, W. -H.; Chan, A. S. C. J. Am. Chem. Soc. 1999, 121, 7407. (b) Chan, A. S. C.; Fan, Q. H. US Patent 5990318, 1999.
[6] a) Fan, Q. H.; Li, Y. M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3467; (b) Cole-Hamilton, D.J. Science. 2003, 299, 1702.
[7] Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369.
[1].For reviews of supported chiral catalysts, see: (a)Bergbreiter,D.E .Chem.Rev.2002,102,3345. (b)Leadbeater,N.E .;M arco,M .Chem.Rev.2002,102,3217. (c)McNamara,C.A .;Dixon,M.J. ;Bradley,M .Chem.Rev.2002,102,3275. (d)Dickerson,T.J .;Reed,N.N .;Ja nda,K .D .Chem.Rev.2002,102,3325. (e).Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P.W N. M .Angew.C hem.Int.Ed 2001,40,1828 (f)Astruc,D .;Chardac,F .Chem.Rev.2001,101,2991. (g)van Heerbeek, R.; Kamer, P.C. J.; van Leeuwen, P.W.N.W.; Reek, J. N. HChem.Re v.2002,102,37 17
[2]For reviews of inorganic material-immobilized chiral catalysts, see: (a).S ong,C .E .;L ee,S . hem.Rev.2002,102,3495. (b).F an,Q .H.;L i,Y .M.;Chan,A .S .C .Chem.Rev.2002,102,3385. (c).Vos,D .E .D.;D ams,M .;Sels,B.F.;Jacobs,P.A.Chem.Rev.2002,102,3615
[3](a).B reysse,E .;Pinel,C.;Lemaire,M .Te trahedron:Asymmetry 1998,9,897. (b).Locatelli,F.;Gamez,P.;Lemaire,M .J.Mol.Catal.A:Chem.1998,135,89. (c).Polborn,K .;Severin,K.Chem.Commun.1999,2481. (d).Pclbom,.;Severin,K .Chem.Eur.J2000,6,4604. (e).Polbonr,K.;S everin,K .;E ur.J.Inorg.Chem.2000,1687 (f)Touchard,F. ;Fa che,F. ;Lemaire,M.Eur.J.Org.Chem.2000,3787. (g). Rolland, A.; Herault, D.;Touchard, F.; Saluzzo, C.; Duval, R.; Lemaire, M.Tetrahedron: Asymmetry 2001, 12, 811.
[4] (a)Adima,A .;Moreau,J. J .E .;Man,M .W .C .J Mater.Chem.,1997,7,2331. (b) .Adima,A .;Moreau,J. J. E .;M an,M .W .C .Chiraliry., 2000,12 ,411. (c). Hesemann,P. ;Moreau,J. J. E .Tetrahedron:Asymmetry2000,11 ,2183.
[5]Sandee,A .J. ;Petra,D .G .1. ;R eek,J .N .H .;K amer,PC.J. ;v anLeeuwen,PW.N . M. C he m.E ur.J 2001,7, 1202.
[6] (a).H ashiguchi,S .;F ujii,A .;T akehara,J .;lk ariya,T .;N oyori,R .J.A m.Chem.Soc.1995, 117,7562.(b) Fujii, A .;H ashiguchi,S. ;U ematsu,N .;lk ariya,T .;N oyori,R .J.Am.Chem.Soc.,1996, 118,2521.(c) Haack,K .J.;Hashiguchi,S .;F ujii,A .;Ik ariya;Noyori,R .A ngew.Chem.Int.Ed .Eng l.1997,36 ,285.(d) Mat sumura,K .;Hashiguchi,S .;Ikariya,T .;Noyori,R .J.Am.Chem.Soc.1997,119 (e) Noyori,R .;Hashiguchi,S.A cc.Chem.Res.1997,30,97.(f)Watanabe,M .;M urata,K ;lkariya,T. J. Org.Chem.2002,67,1712.
[7]Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9,2015 .
[8](a) Li, H. X.; Zhang, F.; Wan, Y.; Lu, Y. F. J. Phys. Chem. B: 2006, 110, 22942. b) Wan, Y.; Zhang, F.; Lu, Y. F.; Li, H. X. J. Mol. Catal. A: Chem. 2007, 267, 165. c) Wan, Y.; Chen, J.; Zhang, D. Q.; Li, H. X. J. Mol. Catal. A: Chem. 2006, 258, 89)。
[9] (Kr?cher, O.; K?ppel, R. A.; Fr?ba, M.; Baiker, A. J. Catal. 1998, 178, 284-298.)
[10](a) Li, H. X.; Zhang, F.; Wan, Y.; Lu, Y. F. J. Phys. Chem. B: 2006, 110, 22942. b) Wan, Y.; Zhang, F.; Lu, Y. F.; Li, H. X. J. Mol. Catal. A: Chem. 2007, 267, 165.
[11]Chong, A. S. M.; Zhao, X. S. J. Phys. Chem. B: 2003, 107, 12650-12657.
[12]Hu, Q. Y.; Hampsey, J. E.; Jiang, N.; Li, C. J.; Lu, Y. F. Chem. Mater. 2005, 17, 1561-1569.
[13]Burkett, S. L.; Sims, S. D.; Mann, S. Chem. Commun. 1996, 1367-1368.
[14]a) Fowler, C. E.; Burkett, S. L.; Mann, S. Chem. Commun. 1997, 1769-1770. b) Zeidan, R. K.; Dufaud, V.; Davis, M. E. J. Catal. 2006, 239, 299-306.
[15]Zhao,D.;Huo,Q.;Feng,J.;Chmelka,B.F.;Stucky,G.D.J.Am.Chem.Soc.1998,120, 6024-6036.
[16]a)Mbaraka,I.K.;Shanks,B.H.J.Catal.2005, 229,365.b)Stein,A.;Lim,M.H.Chem.Mater.1999, 11, 3285
[17]S.A.Bagshaw,E.Prouzet,T.J.Pinnavaia,“Templating of mesoporous molecular sieves by nonionic polyethylene oxide surfactants”.Science,1995,269:1242-1244.
[18]P.T.Tanev,T.J.Pinnavaia,“Mesoporous silica molecular sieves prepared by ionic and neutral surfactant templating:A comparison of physical properties”,Chem.Mater.,1996,8:2068-2079.
2. Noyori, R. J. Am. Chem. Soc. 1987, 109, 5856.
3. Jacobsen, E. N. Tetrahedron. 1994, 50, 4323.
4. Pritchett, S.; Woodmansee, D. H.; Davis, T. J.; Waksh, P. J. Tetrahedron Lett. 1998, 39, 5941.
5. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
6.Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem. Chem. Int. Engl. 1997, 36, 1871.
7. Mikami,K.;Terada,M.;Nakai,T., Chem.Express, 1989, 4, 589
8. Noyori,R.;Tomino,l.;Tanimoto,Y ., J.Am.Chem.Soc., 1979, 101, 3129.
9. (a) Kagan,H .B .;Riant,O., Chem.Rev., 1992, 92 ,1007. (b) Mikami,K .;Shimizu,M ., Chem .Rev., 1992, 92, 1021. (c) Noyori,R.Asymmetric Catalysisin Organic Synthesis;Wiley and Sons: New York, 1994.
10.(a) Artz, S. P.; DeGrandpre, M. P.; Cram, D. J., J. Org. Chem., 1985, 50, 1486. (b) Ohki,A.;Miyashita,R .;Naka,K .;Maeda,S. ,Bull. Chem.Soc.Jpn, 1991, 64 ,2714
11. Maruoka,K .;Itoh,T.;Shirasaka,T.;Yamamoto,H ., J. Am.Chem.Soc, 1998, 110, 310.
12. (a) Hawkins, J. M.; Loren, S.; Nambu, M., J. Am. Chem. Soc., 1994, 116, 1657. (b) Aggarwal,V .K .;Anderson,E .;Giles,R .;Zaparucha,A ., Tetrahedron:Asymmetry 1995, 6, 1301. (c) Ishihara,K .;Yamamoto,H .,J. Am.Chem.Soc, 1994, 116, 1561.
13. (a) Ishihara, K.; Kurihara, H.; Yamamoto, H., J. Am. Chem. Soc., 1996, 118, 3049 (b) Ish ih ara,K.; Kurihara, H.; Matosumoto, M.; Yamamoto, H., J.Am, Chem. Soc, 1998, 120 , 6920. (c) Ishihara, K .;Kondo,S.; Kuirhara,H.; Matosumoto, M.; Yamamoto, H., J. Org. Chem., 1997, 62, 3026. (d) Yamamoto,H .;Yanagisawa,A ;Ishihara,K ;Saito,S ., Pure Appl.Chem., 1998, 70 ,1507.
14.Sasai, H .; Tokunaga, T .; Watanabe, S .; Suzuki, T ; Itoh, N; Shibasaki, M., J. Org. Chem. 1995 , 60, 7388
15. For dierct catalytic asymmetirca aldol reaction see:Yoshikawa,N.; Yamada,Y. M. A; Das, J.; Sasai, H .;Shibasaki,M .,J.Am.Chem.Soc.,1999,121,4168
16. Ding,K .L .;Ishii,A .;Mikami,K .,Angew.Chem.,Int.Ed .,1999,20 ,65 .
17.Mikami,K .;Ding,K .L.;Ishii,A .;Tanaka,A .;Sawada}N .;Kudo,K .,Chromatography,1999 ,20,65.
18.(a)Shibasaki,M .;Sasai,H .;Ara,T.,Angew.Chem.,Int.Ed.,1997,36,1236. (b)Shibasai,M.;Sasai,H.;Arai,T .;Iida,T .,Puer.Appl.Chem.,1998,70,1027. (c)Shibasaki,M .;Gorger, H .T .,Organomet.Chem.,1999,2, 199.
19.Yamada,K .;Harwood,S.J. ;Gorger,H ;Shibasaki,M .,Angew.Chem., Int. Ed., 1999, 38, 3504.
20.Nemoto,T .;Ohshima,T .;Yamaguchi,K .;Shibasaki,M .,J.Am.Chem.Soc.,2001,1233725 .
21.(a)Gao,G .;Moore,D .;Xie,R .-G.;Pu ,L. ,Org.Lett.,2002,4(23),4143.4146. (b)Moore,D.; Pu ,L .,Org.Lett.,2002,4(11),1855-1857.
22.Gao,G .;Xie,R- -G.;Pu ,L. ,PN AS,20 04,10 1(15),5417-5420.
23.S.Hashiguch,A.Fujii,J.Takehara,et.al,, J.Am.Chem.Soc., 117,7562(1995 )
24. T.Langer,G.Helmchen,Tetrahedron Letters,37,1987 (1996).
25. (a)J.X.Gao,T.Ikariya,R.Noyori,Organometallics,15,1087(1996);
26 .C.Botteghi,et.al,J.Organomet.Chem.304 ,217(1986)
27. S.Yamaguchi,et.al.,Tetrahedron:Asymmetry,4,143(1993)
28. G.Zassinovich,et.al.,J.Mol.Catal.,42,81(1987).
29. G.Zassinovich,et.al.,J.Organomet.Chem.,370,187(1989)
30. G.Mestroni,et.al., J.Mol.Catal.,l18,33(1983)
31. Guohua Liu, Mei Yao, Fang Zhang, Yan Gao and Hexing Li.,Chem. Commun., 2007, 1–4
32. Nathaniel,J.;Alcick.Tetrahydron Asymmetion 2002,13,2485-2490.
33. Ekkehard.Lindner.,Inorganic.Chemica.Acta.2003,350,49-56.
34. S.Fiorilli,B.Onida,B.Bonelli,E.Garrone,j.Phys.Chem.B,2005,109:16725-16729.
35. GM.Schwab, FRost,L. Rudolph , Kolloold-Zeitschrif 1934 , 68 , 157
36. D.Lipkin,TD.Stewart,J.Am.Chem .Soc.,1939,61,3297
37. W A .Herrmann.,C.W Kohlpaintner, Angew.Chem.Int.Ed.Eng,1993,32,1524
38. R.Selke, M.Capka, J.Mol.Catal.1990, 63, 319.
39. A.Vaccari.,Catal.Today.,1998,41,53.
40.李晓红,李灿,化学进展,2003 , 15, 204.
41.(a)K.T.Wan,M.E.Davis,J.Catal,1995,152,25.,(b)K.T.Wan,M.E.Davis,Nature.1994 ,370
42.马红霞,四川大学博士论文.2003 ,
43.Ohkuma, H Takeno,Y Honda , R Noyori-Adv.Synth.Catal .2001,343,369
44.(a)S.Itsuno,M.Takahashi,A.Tsuji,MacromL.Symp.,2004,217,191.; (b)S.ItsA.Tsuji,M.Takahashi,J.Polymer.Science.,2004,42,4556.; (c)S.Itsuno,M.Takahash.Tsuji,Tetrahedron .Lett.2003,44,3825.
45. A.Hu,H.L.Ngo,WB. Liu, J.Am.Chem.Soc.2003,125,11490.
46. P.Liu,P.Gu, F.Wang, YQ.Tu, Org.Letters,2004,6,169
47 Bayston,D.J.;Travers,C.B.;Pobnvka,M.E.C.Tetrahedron:Asymmetry 1998,9,2015.
48 Adima,A.;Moreau ,J.J.E. ;Chi Man,M.W.Chirality.2000,12,411.
49 B. F. G.Johnson, S. A. Raynor, D. S. Shephard, T. Mashmeyer, J. M. Thomas, G. Sankar, S. BromLey, R. Oldroyd, L. Gladden, M. D. Mantle,“Superiorperformance of a chiral catalyst confined within mesoporous silica”, Chem. Commun., 1999, 1167.
50 P.N.Liu,J.G.Deng,Y.Q.Tu,S.H.Wang,“Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in water”, Chem.Commun., 2004, 2070.
51 P.N.Liu,P.M.Gu,F.Wang,Y.Q.Tu,“Efficient heterogeneous asymmetric transfer hydrogenation of ketones using highly recyclable and accessible silica-immobilized Ru-TsDPEN catalysts”,Org.Lett., 2004, 6:169
52 Sanchez C,Ribot F,Organic/inorganic hybrid materials,NewJ.Chem., 1994, 18(22)1007-1047.
53.Luan, Z.;Cheng, C.F.; Zhou,W; Klinoski, J.J.Phys.Chem .1995.99, 1018.
54 .Fu, G.;Fyfe, C.A.;Schwieger, W .Kokotaill, G. Angew. Chem.,Int.Ed.Eng. 1995, 34, 1499.
55.Fyfe,C.A;Fu,G..J.Am.Chem.Soc.1995, 117, 9709.
56 Takeguchi,T.;Kim,J.B.;Kang,M.;Inui,T.;Cheuh,W.T.;haller,G.L.J.Catat. 1998, 175
57 Sayari,A.;Danumah,C.;Moudarkoski,I.L.Chem.Mater 1995, 7,813
58 Zhang,M.;Fr?b,M.;Wang,J.Tanev,P.T.;Wong,J.; J.Am.Chem.Soc.1996,118,9164
59 Blasco,T,; Corma,A;Navarro,M.T.;Pariete,J. P.J .Catal. 1995 , 156, 65
60 Alba,M.A .;Luan,Z;Klinowski, J.J.Phys.Chem.1996, 100, 2178.
61Wei,D.;wang,H.;Feng,X.;Chueb,W.-T.;Ravikovitch,P.;Lyubovsky,M.;Li,C;takeduchi,T.;haller,G.L.J.Phys.Chem.B.1998,103,2113.
62 Chatterjee,M.;Iwasaki,T.;Hayashi,H.;Onodera,Y;Ebina,; Chem.Mater.1999, 11, 1368.
63 Zhao,D.;Goldfarb,D.J.Chem.Soc.Chem.Commun.1995,875,
64 a) Tuan, B. Z.; Tu, B.; Zhao, D. Y. Nature Materials, 2003, 2, 159. b) Xiao, F. S. J. Am. Chem. Soc., 2002, 122, 888.
65 Zheng, S.; Gao, L.; Guo, J. Mater. Chem. Phys., 2001, 71, 174.
66 De Vos, D. E.; Dams, M.; Sels, B. F.; Jacobs, P. A. Chem. Rev. 2002, 102, 3615.
67 Raynor, S. A.; Thomas, J. M.; Raja, R.; Johnson, B. F. G.; Bell, R. G.; Mantle, M. D. Chem. Commun. 2000, 1925.
68 de Rege, F. M.; Morita, D. K.; Ott, K. C.; Tumas, W.; Broene, R. D. Chem. Commun. 2000, 1797.
69 a) B. F. G. Johnson, S. A. Raynor, D. S. Shepard, T. Mashmeyer, J. M. Thomas, G. Sankar, S. BromLey, R. Oldroyd, L. Gladden, M. D. Mantle, Chem. Commun. 1999, 1167; b) B. Pugin, H. Landert, F. Spindler, H. U. Blaser, Adv. Synth. Catal. 2002, 344, 974; d) M. J. Alcón, A. Corma, M. Iglesias, F. SZnchez, J. Organomet. Chem. 2002, 655, 134. c) P. N. Liu, P. M. Gu, F.Wang, Y. Q. Tu, Org. Lett. 2004, 6, 169; b] P.-N. Liu, P.-M. Gu, J.-G. Deng, Y.-Q. Tu, Y.-P. Ma, Eur. J. Org. Chem. 2005, 3221. d) P. N. Liu, J. G. Deng, Y. Q. Tu, S. H. Wang, Chem. Commun. 2004, 2070.
70a) Jiang, D. M.; Yang, Q. H., Yang, J.; Zhang, L.; Zhu, G. R.; Su, W. G.; Li, C. Chem. Mater. 2005, 17, 6154-6160. b) Jiang, D. M.; Gao, J. S.; Qihua Yang, Q. H.; Yang, J.; Li, C. L. Chem. Mater. 2006, 18, 6012-6018.
71 Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369.
72 Knowles, W. S.; Sabacky, M. J. U. S. Patent 3849480, 4005127, 4142992, 4220590.
73 Knowles, W. S. J. Chem. Educ. 1968, 63, 222. 67.
74 Chan, A. S. C. CHEMYTECH. 1993, 23, 46.
[1] 孙健,胡文浩,具有C:对称轴的手性配体及其不对称催化反应,合成化学,1995,3(1):1 9-28.
[2] Pu L. 1,1'-binaphthyl dimers, oligomers, and polymers:molecular recognition, asymmetric cat aly sis ,an dn ewm aterials[J].Chem.Rev.,1998,98:2405-2494.
[3] 郭红超,王敏。联蔡衍生物作为手性配体在不对称氢化中的应用,2000,20 ( 4 ):486-498
[4] Fan, Q. -H.; Deng, G. -J.; Lin, C. -C.; Chan, A. S. C. Tetrahedron: Asymmetry . 2001, 12, 1241.
[5] (a) Fan, Q. -H.; Ren, C. -Y.; Yeung, C. -H.; Hu, W. -H.; Chan, A. S. C. J. Am. Chem. Soc. 1999, 121, 7407. (b) Chan, A. S. C.; Fan, Q. H. US Patent 5990318, 1999.
[6] a) Fan, Q. H.; Li, Y. M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3467; (b) Cole-Hamilton, D.J. Science. 2003, 299, 1702.
[7] Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369.
[1].For reviews of supported chiral catalysts, see: (a)Bergbreiter,D.E .Chem.Rev.2002,102,3345. (b)Leadbeater,N.E .;M arco,M .Chem.Rev.2002,102,3217. (c)McNamara,C.A .;Dixon,M.J. ;Bradley,M .Chem.Rev.2002,102,3275. (d)Dickerson,T.J .;Reed,N.N .;Ja nda,K .D .Chem.Rev.2002,102,3325. (e).Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P.W N. M .Angew.C hem.Int.Ed 2001,40,1828 (f)Astruc,D .;Chardac,F .Chem.Rev.2001,101,2991. (g)van Heerbeek, R.; Kamer, P.C. J.; van Leeuwen, P.W.N.W.; Reek, J. N. HChem.Re v.2002,102,37 17
[2]For reviews of inorganic material-immobilized chiral catalysts, see: (a).S ong,C .E .;L ee,S . hem.Rev.2002,102,3495. (b).F an,Q .H.;L i,Y .M.;Chan,A .S .C .Chem.Rev.2002,102,3385. (c).Vos,D .E .D.;D ams,M .;Sels,B.F.;Jacobs,P.A.Chem.Rev.2002,102,3615
[3](a).B reysse,E .;Pinel,C.;Lemaire,M .Te trahedron:Asymmetry 1998,9,897. (b).Locatelli,F.;Gamez,P.;Lemaire,M .J.Mol.Catal.A:Chem.1998,135,89. (c).Polborn,K .;Severin,K.Chem.Commun.1999,2481. (d).Pclbom,.;Severin,K .Chem.Eur.J2000,6,4604. (e).Polbonr,K.;S everin,K .;E ur.J.Inorg.Chem.2000,1687 (f)Touchard,F. ;Fa che,F. ;Lemaire,M.Eur.J.Org.Chem.2000,3787. (g). Rolland, A.; Herault, D.;Touchard, F.; Saluzzo, C.; Duval, R.; Lemaire, M.Tetrahedron: Asymmetry 2001, 12, 811.
[4] (a)Adima,A .;Moreau,J. J .E .;Man,M .W .C .J Mater.Chem.,1997,7,2331. (b) .Adima,A .;Moreau,J. J. E .;M an,M .W .C .Chiraliry., 2000,12 ,411. (c). Hesemann,P. ;Moreau,J. J. E .Tetrahedron:Asymmetry2000,11 ,2183.
[5]Sandee,A .J. ;Petra,D .G .1. ;R eek,J .N .H .;K amer,PC.J. ;v anLeeuwen,PW.N . M. C he m.E ur.J 2001,7, 1202.
[6] (a).H ashiguchi,S .;F ujii,A .;T akehara,J .;lk ariya,T .;N oyori,R .J.A m.Chem.Soc.1995, 117,7562.(b) Fujii, A .;H ashiguchi,S. ;U ematsu,N .;lk ariya,T .;N oyori,R .J.Am.Chem.Soc.,1996, 118,2521.(c) Haack,K .J.;Hashiguchi,S .;F ujii,A .;Ik ariya;Noyori,R .A ngew.Chem.Int.Ed .Eng l.1997,36 ,285.(d) Mat sumura,K .;Hashiguchi,S .;Ikariya,T .;Noyori,R .J.Am.Chem.Soc.1997,119 (e) Noyori,R .;Hashiguchi,S.A cc.Chem.Res.1997,30,97.(f)Watanabe,M .;M urata,K ;lkariya,T. J. Org.Chem.2002,67,1712.
[7]Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9,2015 .
[8](a) Li, H. X.; Zhang, F.; Wan, Y.; Lu, Y. F. J. Phys. Chem. B: 2006, 110, 22942. b) Wan, Y.; Zhang, F.; Lu, Y. F.; Li, H. X. J. Mol. Catal. A: Chem. 2007, 267, 165. c) Wan, Y.; Chen, J.; Zhang, D. Q.; Li, H. X. J. Mol. Catal. A: Chem. 2006, 258, 89)。
[9] (Kr?cher, O.; K?ppel, R. A.; Fr?ba, M.; Baiker, A. J. Catal. 1998, 178, 284-298.)
[10](a) Li, H. X.; Zhang, F.; Wan, Y.; Lu, Y. F. J. Phys. Chem. B: 2006, 110, 22942. b) Wan, Y.; Zhang, F.; Lu, Y. F.; Li, H. X. J. Mol. Catal. A: Chem. 2007, 267, 165.
[11]Chong, A. S. M.; Zhao, X. S. J. Phys. Chem. B: 2003, 107, 12650-12657.
[12]Hu, Q. Y.; Hampsey, J. E.; Jiang, N.; Li, C. J.; Lu, Y. F. Chem. Mater. 2005, 17, 1561-1569.
[13]Burkett, S. L.; Sims, S. D.; Mann, S. Chem. Commun. 1996, 1367-1368.
[14]a) Fowler, C. E.; Burkett, S. L.; Mann, S. Chem. Commun. 1997, 1769-1770. b) Zeidan, R. K.; Dufaud, V.; Davis, M. E. J. Catal. 2006, 239, 299-306.
[15]Zhao,D.;Huo,Q.;Feng,J.;Chmelka,B.F.;Stucky,G.D.J.Am.Chem.Soc.1998,120, 6024-6036.
[16]a)Mbaraka,I.K.;Shanks,B.H.J.Catal.2005, 229,365.b)Stein,A.;Lim,M.H.Chem.Mater.1999, 11, 3285
[17]S.A.Bagshaw,E.Prouzet,T.J.Pinnavaia,“Templating of mesoporous molecular sieves by nonionic polyethylene oxide surfactants”.Science,1995,269:1242-1244.
[18]P.T.Tanev,T.J.Pinnavaia,“Mesoporous silica molecular sieves prepared by ionic and neutral surfactant templating:A comparison of physical properties”,Chem.Mater.,1996,8:2068-2079.