链状L-氨基酸的N-手性季铵盐研究
|
摘要
本论文主要对链状L-氨基酸的N-手性季铵盐进行了研究,包括N-手性季铵盐的合成、分离、N-手性绝对构型的确定,并对它们的稳定性等进行了考察。本论文包括三部分:
◆N-手性季铵盐的合成及其在有机合成中的应用(综述)
本文对N-手性的发现、N-手性季铵盐的合成、分离、绝对构型确定及其在有机合成中应用进行了简要综述。
◆链状L-氨基酸的N-手性季铵盐的合成、分离、及绝对构型确定
对合成叔胺的“一锅法”进行了改进,并成功合成了12对新的链状和环状N-手性季铵盐。
采用手性联萘酚包结拆分法、重结晶法、沉淀法等成功地对其中9对N-手性季铵盐的非对映异构体混合物进行了分离,通过X-单晶衍射确定了其中16个N-手性季铵盐中N的绝对构型。
◆N-手性季铵盐的取代反应、不对称催化及稳定性研究
链状L-氨基酸合成N-手性季铵盐过程中发现的N上基团被烯丙基取代现象为首次发现。对反应进行了初步考察,其过程是先生成了预期的季铵盐,随后这个季铵盐中的基团又被烯丙基溴取代。
初步实验表明,底物中带有甲氧羰基及卤代烃为烯丙基溴对于此取代现象是必要的。
初步实验表明,我们所合成的N-手性季铵盐显示出一定程度不对称催化作用,但是选择性不高;所合成的N-手性季铵盐对光、热及酸碱稳定,未发现消旋化。
This dissertation aims at the studies on N-chiral quaternary ammonium salts (QASs)of linear L-amino acid,including the syntheses,separation,the absolute configuration determination of N-chirality,and their stablity.It consisted of the following three parts:
The syntheses and applications of N-chiral QASs in organic syntheses (Riview)
Described the finding,syntheses,separation,the absolute configuration determination and applications of N-chiral QASs in organic syntheses.
Studies on N-chiral QASs of linear L-amino acid,including the syntheses, separation,the absolute configuration determination of N-chirality.
We synthesized tertiary amine using improved“one pot”method from linear L-amino acid,and synthesized twelve paries of linear and cyclic N-chiral QASs successfully.
We separated nine pairs of these QASs diastereomers through resolution by chiral BINOL,recrystallization,precipitation and determined the absolute configuration of N-chirality by X-ray single crystallographic analysis for sixteen of them.
Studties on the substitute reaction,asymmetric catalyzed reaction and the stability of N-chiral QASs
In the course of synthesis of N-chiral QASs from L-amino acids,when the tertiary amine with a methoxycarbonyl group refluxed with allyl bromide in CH_3CN, diallyl substitued QASs were obtained instead of the expected N-chiral QASs.We studied the reaction conditions such as various substrates,temperature,halogenated hydrocarbon.We believe that the required N-chiral QASs were formed firstly,then they reacted with allyl bromide quickly to obtain the diallyl substitued QASs.
The preliminary experiments indicated that the tertiary amine with a methoxy car-bonyl group and the allyl bromide are necessary for the substitute.
The preliminary experiment indicated that the N-chiral QASs have a certain extent asymmetric catalyzed activity,but the selectivity is not high.There is no racemization when N-chiral QASs under light,hot,acid and base
◆N-手性季铵盐的合成及其在有机合成中的应用(综述)
本文对N-手性的发现、N-手性季铵盐的合成、分离、绝对构型确定及其在有机合成中应用进行了简要综述。
◆链状L-氨基酸的N-手性季铵盐的合成、分离、及绝对构型确定
对合成叔胺的“一锅法”进行了改进,并成功合成了12对新的链状和环状N-手性季铵盐。
采用手性联萘酚包结拆分法、重结晶法、沉淀法等成功地对其中9对N-手性季铵盐的非对映异构体混合物进行了分离,通过X-单晶衍射确定了其中16个N-手性季铵盐中N的绝对构型。
◆N-手性季铵盐的取代反应、不对称催化及稳定性研究
链状L-氨基酸合成N-手性季铵盐过程中发现的N上基团被烯丙基取代现象为首次发现。对反应进行了初步考察,其过程是先生成了预期的季铵盐,随后这个季铵盐中的基团又被烯丙基溴取代。
初步实验表明,底物中带有甲氧羰基及卤代烃为烯丙基溴对于此取代现象是必要的。
初步实验表明,我们所合成的N-手性季铵盐显示出一定程度不对称催化作用,但是选择性不高;所合成的N-手性季铵盐对光、热及酸碱稳定,未发现消旋化。
This dissertation aims at the studies on N-chiral quaternary ammonium salts (QASs)of linear L-amino acid,including the syntheses,separation,the absolute configuration determination of N-chirality,and their stablity.It consisted of the following three parts:
The syntheses and applications of N-chiral QASs in organic syntheses (Riview)
Described the finding,syntheses,separation,the absolute configuration determination and applications of N-chiral QASs in organic syntheses.
Studies on N-chiral QASs of linear L-amino acid,including the syntheses, separation,the absolute configuration determination of N-chirality.
We synthesized tertiary amine using improved“one pot”method from linear L-amino acid,and synthesized twelve paries of linear and cyclic N-chiral QASs successfully.
We separated nine pairs of these QASs diastereomers through resolution by chiral BINOL,recrystallization,precipitation and determined the absolute configuration of N-chirality by X-ray single crystallographic analysis for sixteen of them.
Studties on the substitute reaction,asymmetric catalyzed reaction and the stability of N-chiral QASs
In the course of synthesis of N-chiral QASs from L-amino acids,when the tertiary amine with a methoxycarbonyl group refluxed with allyl bromide in CH_3CN, diallyl substitued QASs were obtained instead of the expected N-chiral QASs.We studied the reaction conditions such as various substrates,temperature,halogenated hydrocarbon.We believe that the required N-chiral QASs were formed firstly,then they reacted with allyl bromide quickly to obtain the diallyl substitued QASs.
The preliminary experiments indicated that the tertiary amine with a methoxy car-bonyl group and the allyl bromide are necessary for the substitute.
The preliminary experiment indicated that the N-chiral QASs have a certain extent asymmetric catalyzed activity,but the selectivity is not high.There is no racemization when N-chiral QASs under light,hot,acid and base
引文
[1]Blaschke,G..;Kraft,H.P.;Markgraf,H.Chem.Ber.1980,113,2318.
[2](a)殷元骐,蒋耀忠,不对称催化反应进展,科学出版社,2000;
(b)林国强,陈耀全,陈新滋,李月明,手性合成不:对称反应及其冱用,科学出版社,2000;
(c)尤启东,林国强,手性药物-研究与应用,化学工业出版社,2004。
[3](a)Shioiri,T.in Handbook of Phase-Transfer Catalysis(Eds.:Y.Sasson,R.Neumann),Blackie Academic & Professional,London,1997,chap.14;
(b)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1998,4,5;
(c)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1999,5,5;
(d)Nelson,A.Angew.Chem.1999,111,1685;Angew.Chem.Int.Ed. 1999,38,1583;
(e)Shioiri,T.;Arai,S.in Stimulating Concepts in Chemistry (Eds.:Vogtle,F.;Stoddart,J.F.;Shibasaki,M.),Wiley-VCH,Weinheim,2000,p.123;
(f)O'Donnell,M.J.in Catalytic Asymmetric Syntheses,2nd ed.(Ed.:I.Ojima),Wiley-VCH,New York,2000,chap.10;
(g)O'Donnell,M.J.Aldrichimica Acta 2001,34,3;
(h)Maruoka,K.;Ooi,T.Chem.Rev.2003,103,3013;
(i)O'Donnell,M.J.Acc.Chem.Res.2004,37,506;
(j)Lygo,B.;Andrews,B.I.Acc.Chem.Res.2004,37,518.
[4](a)沈宗旋,孔爱娣,陈文勇,张雅文 有机化学,2003,23(1),10;
(b)张占辉,河北师范大学学报(自然科学版),2004,28(6),608;
(c)宓爱巧,楼荣良,蒋耀忠合成化学,1996,4(1),13.
[5]Ooi,A.;Maruoka,K.Angew.Chem.Int.Ed.2007,46,4222.
[6]Ooi,T.;Kameda,M.;Maruoka,K.J.Am.Chem.Soc.1999,121,6519.
[7]For recent reviews,see:
(a)Denissoval,I.;Barriault,L.Tetrahedron 2003,59,10105;
(b)Rlant,O.;Hannedouche,J.Org.Biomol.Chem.2007,5,873;
(c)Kaoru F.Chem.Rev.1993,93,2037.
[8]For recent reviews,see:
(a)Molt,O.;Schrader,T.Synthesis 2002,2633;
(b)Chelucci,G.;Orru,G.;Pinna,G.A.;Tetrahedron 2003,59,9471;
(c)Tang,W.;Zang,X.Chem.Rev.2003,103,3029.
[9]For recent reviews,see:
(a)Mellah,M.;Voituriez,A.;Schulz,E.Chem.Rev.2007,107,5133;
(b)Allenmark,S.Chirality 2008,20,544.
[10]Le Bel Compt.Rend.1891,112,724.
[11]Marckwald,von Droste-Huelshoff Ber.1899,32,560
[12]Wedekind Ber.1899,32,517.
[13]Kauffman,G.B.J.Chem.Educ.1972.49.813.
[14]Vsn't Hoff.J.H.MaondbloduoorNotuunuefansehopppn 1877,7,1W:Ansi-chtonirber die orgonimhs Chomio;Vimeg:Braunschwek,1876,80.
[15](a)Wilkerdt,C.J.Prokf.Chrm.1888,(2)37,449;
(b)1890,(2)41,291.
[16](a)Werner,A.Z.anorg.Chem.1893,3,267;
(b)translated into English with commentary as “Contribution to the Constitution of Inorganic Compounds” in Kanuffman,G.B.Classics in Coordinofion Chemlafrv.Part 1: The Selected Papers of Alfred Werner: New York, 1966: pp 9-88.
[17]Kauffman, G.B.Naturwiss.1976, 63, 324.
[18]Pope, W.J.; Peachey, S.J.J.Chem.Soc.1899,1127.
[19](a) Jones, H.0.J.Chem.Soc.1904, 85, 223; (b) Thomas, M.B.; Jones, H.0.J.Chem.Soc.1906, 89, 280; (c) Jones, H.O.; Hill, J.R.J.Chem.Soc.1908, 93,295; (d) Wedckind, E.; Frohlich, E.Ber.1905,36,3438; 1907,40,1001; (e)Frohlich, E., Wedekind.E.Ber.1907,40,1646; (f) Wedekind, B.; Wedekind, O.Ber.1907, 40, 4450; (g) Wedekind, E.; Mayer, W.Ber.1909.42.303; (h)Everatt,R.W.7.Chem.Soc.1908, 93,1225.
[20](a) Mills, W.H.; Warren, E.H./.Chem.Soc.1925.127, 2507; (b) Mills, W.H.;Bains, L.J.Chem.Soc.1925,127, 2502.
[21]Wyckoff, W.G.; Pasnjek.E.J.Am.Chem.Sor.1921.43.2292; reprinted with annotations in Kauffman, G.B.Classics in Coordimtion Chemistry, Part 3:Twentieth- Century Papers (1904-1935): Dover: New York.1978: pp 89-111.
[22]Recently, the absolute configuration was determined by a single crystal X-ray diffraction, see: Torbeev, V.Y.; Lyssenko, K.A.; Kharybin, O.N.; Antipin, M.Y.; Kostyanovsky, R.G.J.Phys.Chem.B 2003,107,13523.
[23]Kacprzak, K.; Gawronski, J.Synthesis 2001, 961.
[24]Dolling, U.-H.; Davis, P.and Grabowski, E.J.J.J.Am.Chem.Soc.1984,106,446.
[25]O'Donnell, M.J.; Wu, S.; Huffman, J.C.Tetrahedron, 1994,50,4507.
[26]Lygo, B.; Wainwright, P.G Tetrahedron Lett.1997, 38, 8595.
[27]Corey, E.J.; Xu, F.; Noe, M.C.J.Am.Chem.Soc, 1997,119,12414.
[28]Lygo, B.; Crosby , J.; Lowdon, T.R.; Wainwright, P.G.Tetrahedron 200157, 2391.
[29]Chinchilla, R.; Mazon, P.; Nojera, C.Tetrahedron: Asymmetry 2002,13, 927.
[30]Park, H.G; Jeong, B.S.; Yoo, M.S.et al.Tetrahedron Lett.2001,42, 4645.
[31]Thierry, B.; Plaquevent, J.C; Cahard, D.Tetrahedron .Asymmetry 2001,12,983.
[32](a)Von Matus,R.;Kreh,M.;M(u|¨)ller,U.Helv.Chim.Acta.1994,77,1611;
(b)Eddine,J.J.;Cherqaoui,M.Tetrahedron:Asymmetry 1995,6,1225.
[33]Dehmlow,E.V.;Klauck,R.;Duttmann,S.;Neumann,B.;Stammler,H.-G.Tetrahedron:Asymmetry 1998,9,2235.
[34]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[35]Hill,D.A.;Turner,G.L.1992,US 5453510
[36]Kowtoniuk,W.E.;MacFarland,D.K.;Grover,G.N.Tetrahedron Lett.2005,465703.
[37]Kuma,S.;Sobhi,M.E.;Ramachandran,U.Tetrahedron:Asymmetry 2005,16,2599.
[38]潘英明,唐莅东,王恒山等,有机化学,2006,26,3,349。
[39](a)Diego-Castro,M.J.;Hailes,H.C.Chem.Commun.,1998,1549;
(b)Diego-Castro,M.J.,Hailes,H.C.;Lawrence,M.J.Journal of Colloid and Interface Science 2001,234,122.
[40]Gmouh,S.;Jamal-Eddine,J.;Valnot,J.Y.Tetrahedron 2000,56,8361.
[41]王玉成,陈玉芳,顾 菲,辜顺林 中国新药杂志,2007,19,1599.
[42]Starks,C.M.J.Am.Chem.Soc.1971,93,195.
[43](a)Makosza,M.Pure Appl.Chem.1975,43,439;
(b)Yang,H.-M.;Wu,H.S.Catal.Rev.2003,45,463.
[44]Esikova,I.A.;Nahreini,T.S.;O'Donnell,M.J.in Phase-Transfer Catalysis(Ed.:M.E.Halpern),American Chemical Society,Washington,DC,1997,chap.7(ACS Symposium Series 659);
(d)O'Donnell,M.J.;Esikova,I.A.;Shullenberger,D.F.;S.Wu in Phase-Transfer Catalysis(Ed.:M.E.Halpern),American Chemical Society,Washington,DC,1997,chap.10(ACS Symposium Series 659).
[45]Zheng,Z.G.;Wu,T.H;Zheng,R.W.et al Cata.Commu.2007,8,39.
[46]Wang,W.;Buchholz,A.;Ivanova,I.I.et al Chem.Commu.2003,2600;
(b)Wang,W.;Seiler,M.;Ivanova,I.I.;Sternberg,U.et al J.Am.Chem.Soc.2002,124,7548.
[47]Pleiss,U.;Voges,R.Synthesis and Applications of Isotopically Labelled Compounds, eds.Vol.7, Wiley, New York, 2001, pp.1-728.
[48]Ropponen, J.; Lahtinen,M.; Busi,S.; Nissinen, M.; Kolehmainen, E.; Rissanen, K.New J.Chem.2004, 28,1426.
[49]Sommer, H.Z.; Lipp, H.I.; Jackson, L.L.J.Org.Chem.1971,36,824.
[50]Scarpi, D.; Occhiato, E.G.; Guarna, A.J.Org.Chem.1999,64, 1727.
[51]Smith, P.S.; Tan, H.H.J.Org.Chem.1967,32, 2586.
[52]Glaeske, K.W.; West, F.G.Org.Lett.1999,1,31.
[53]Tayama,E.; Tanaka, H.; Nakai, T.Heterocycles, 2005, 66, 95.
[54]Tayama,E.; Nanbara, S.; Nakai, T.Chem.Lett.2006, 35, 478.
[55]Sasai,H.Jpn.Kokai Tokkyo Koho JP 2006076911.
[56]Hirnschall, M.; Treu, M.; Mereiter, K.; Jordis, U.et al.Tetrahedron: Asymmetry 2003, 14, 675.
[57]Hill, R.K.; Chan, T.-K.J.Am.Chem.Soc.1966, 88, 866.
[58]For an example of transfer of biphenyl dissymmetry to asymmetric carbon in the Stevens rearrangement, see (a) Wittig, G.; Zimmermann, H.Chem.Ber.1953, 86,629; (b) Mislow, K.; Joshua, H.J.Am.Chem.Soc.1965, 87, 666.
[59]Eddine, J.J.; Cherqaoui, M.Tetrahedron: Asymmetry 1995, 6,1225.
[60]Arbore, A.P.A.; Cane-Honeysett, D.J.; Coldham, I.; Middleton, M.L.Synlett.2000, 236.
[61](a) Dehmlow, E.V.; Lissel, M.; Heider, J.Tetrahedron 1977, 33, 363; (b) Dehmlow, E.V.; Singh, P.; Heider, J.J.Chem.Res.(S) 1981, 292; (c) Dehmlow, E.V.; Sleegers, A.J.Org.Chem.1988, 53, 3875.
[1](a)Shioiri,T.in Handbook of Phase-Transfer Catalysis(Eds.:Y.Sasson,R.Neumann),Blackie Academic & Professional,London,1997,chap.14;
(b)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1998,4,5;
(c)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1999, 5,5;
(d)Nelson,A.Angew.Chem.1999 111,1685;Angew.Chem.Int.Ed.1999,38,1583;
(e)Shioiri,T.;Arai,S.in Stimulating Concepts in Chemistry(Eds.:Vogtle,F.;Stoddart,J.F.;Shibasaki,M.),Wiley-VCH,Weinheim,2000,p.123;
(f)O'Donnell,M.J.in Catalytic Asymmetric Syntheses,2nd ed.(Ed.:I.Ojima),Wiley-VCH,New York,2000,chap.10;
(g)M.J.OEDonnell,Aldrichimica Acta 2001,34,3;
(h)Maruoka,K.;Ooi,T.Chem.Rev.2003.103,3013.
(i)O'Donnell,M.J.Acc.Chem.Res.2004,37,506;
(j)Lygo,B.;Andrews,B.I.Acc.Chem.Res.2004,37,518.
[2](a)沈宗旋,孔爱娣,陈文勇,张雅文 有机化学 2003,23(1),10;
(b)张占辉,河北师范大学学报(自然科学版)2004,28(6),608;
(c)宓爱巧,楼荣良,蒋耀忠 合成化学 1996,4(1),13。
[3]Ooi,A.;Maruoka,K.Angew.Chem.Int.Ed.2007,46,4222.
[4]O'Donnell,M.J.;Wu,S.;Huffman,J.C.Tetrahedron 1994,50,4507.
[5]Dehmlow,E.V.;Klauck,R.;Duttmann,S.;Neumann,B.;Stammler,H.-G.Tetrahedron:Asymmetry 1998,9,2235.
[6]von Matusch,R.;Kreh,M.;M(u|¨)ller,U.Helv.Chim.Acta.1994,77,1611.
[7]Hirnschall,M.;Treu,M.;Mereiter,K.;Jordis,U.et al.Tetrahedron:Asymmetry 2003,14,675。
[8]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[9]Pope,W.J.;Peachey,S.J.J.Chem.Soc.1899,1127.
[10]徐春霞,中科院成都生物所硕士学位论文,2005.
[11]李建军,倪爱武,伍新燕,等.科学通报 2002,47(11),837.
[12]Toda,F.;Tanaka,K.;Stein,Z.;Goldberg,I.J.Org.Chem.1994,59,5748.
[13]Wang,Y.;Sun,J.;Ding.K.L.Tetrahedron,2000,56,4447.
[14]umio Toda,Kazuhiro Yoshizawa,Shunji Hyoda,Shinji Toyota,Spyros Chatziefthimiou and Irene M.Mavridis.Organic & Biomolecular Chemistry.2004,2,449.
[15]Ha,W.Z.;Shan,.Z.X.Tetrahedron:Asymmetry 2006,17,854.
[16]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[17]Caira M.R..;Nassimbeni,L.R.,Toda,F.;Vujovic,D.J.Am.Chem.Soc.2000,122,9367.
[18]The Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as deposition No.CCDC-689671(the complex of(NR)-38 and(5)-BINOL),No.CCDC-689672(the complex of(NR)-21 and(S)-BINOL),No.CCDC-689673((NR)-32),No.CCDC-689674((NS)-30),No.CCDC-689675((NR)-39),No.689788(the complex of (NR)-37 and(S)-BINOL),No.CCDC-689789((NR)-33),No.CCDC-689790((NS)-32)and No.CCDC-689791((NS)-34).Copies of the data can be obtained,free of charge,on application to CCDC,12 Union Road,Cambridge CB21EZ,UK[fax:+44(0)4223-336033 or e-mail:deposit@ccdc.cam.ac.uk].
[1]Stohr,C.Bucherschau 1878,477.
[2]Stanger,K.J.;Lee,J.J.;Smith,B.D.J.Org.Chem.2007,72,9663.
[3](a)Sun,H.R.;DiMagno,S.G.Journal of Fluorine Chemistry 2007,128,806;
(b)Baxter,S.J.;Donald B,J.H.;Samuel,C.J.Tetrahedron Letter 1996,37,4617
[4](a)Hofmann,A.W.Ann.1 1851,78,253;
(b)Hofmann,A.W.Ann.1 1851,79,11
[5](a)Hofmann,A.W.Ber.1881,14,659;
(b)Hofmann,A.W.Ber.1881,14,494
[6]Stevens,T.S.;Creighton,E.M.;Gordon,A.B.J.CHEM.Soc.,Aabstracts 1928,3193
[7]Sommelet,M.Compt.Rent.1937,205,56.
[8](a)Bransen,W.R.;Hauser,C.R.Org.Syn.Coll Vol.Ⅳ.1963,508;
(b)Kametani,T.;Kigasawa,K.;Hiiragi,M.;Wagatsuma,N.;Wakisaka,K.Tetrahedron Lett..1969,10,635;
(c)Reich,H.J.;Cohen,M.L.J.Org.Chem.1979,44,3148.
(d)Nicola,M.H.;John,R.M.,Craig R.S.Tetrahedron 1998,54,10899.
(e)Scarpi,D.;Occhiato,E.G.;Guarna,A.J.Org.Chem.1979,44,3148.
[9]Browster,J.B.;Eliel,E.L.In Organic Reactions,Vol.Ⅶ,Roger Adams ed.,John Wiley and Bonn,W.Y.,1853,p.142.
[10]S.Hunig mud W.Baron,Chem.Ber.1957,90,395;1957,90,403.
[11]Glaeske,K.W.;West,F.G.Org.Lett.1999,1,31.
[12]Lygo,B.;Allbutt,B.Synlett 2004,326.
[13]Arai,S.;Tokumaru,T.;Aoyama,T.Tetrahedron lett.2004,45,184
[14]Ooi,T.;Kato,D.;Inamura,K.;Ohmatsu,K.;Maruoka,K.Org.Lett.2007,9,3945
[15]Dehmlow,E.V.;D(u|¨)ttmann,S.;Neumann,B.;Stammler,H.-G.Eur.J.Org.Chem.2002,2087.
[16]Zhang,F.-Y.;Coroy,E.J.Org.Lett.2000,2,1097.
[17]Le Bel Compt.Rend.1891,112,724.
[18]Marckwald,von Droste-Huelshoff Ber.1899,32,560
[19]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[20]Antoni,G.;Langstrom,B.Journal of Labelled Compounds and Radio-phannaceuticals.1986,XXIV(2),125.
[2](a)殷元骐,蒋耀忠,不对称催化反应进展,科学出版社,2000;
(b)林国强,陈耀全,陈新滋,李月明,手性合成不:对称反应及其冱用,科学出版社,2000;
(c)尤启东,林国强,手性药物-研究与应用,化学工业出版社,2004。
[3](a)Shioiri,T.in Handbook of Phase-Transfer Catalysis(Eds.:Y.Sasson,R.Neumann),Blackie Academic & Professional,London,1997,chap.14;
(b)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1998,4,5;
(c)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1999,5,5;
(d)Nelson,A.Angew.Chem.1999,111,1685;Angew.Chem.Int.Ed. 1999,38,1583;
(e)Shioiri,T.;Arai,S.in Stimulating Concepts in Chemistry (Eds.:Vogtle,F.;Stoddart,J.F.;Shibasaki,M.),Wiley-VCH,Weinheim,2000,p.123;
(f)O'Donnell,M.J.in Catalytic Asymmetric Syntheses,2nd ed.(Ed.:I.Ojima),Wiley-VCH,New York,2000,chap.10;
(g)O'Donnell,M.J.Aldrichimica Acta 2001,34,3;
(h)Maruoka,K.;Ooi,T.Chem.Rev.2003,103,3013;
(i)O'Donnell,M.J.Acc.Chem.Res.2004,37,506;
(j)Lygo,B.;Andrews,B.I.Acc.Chem.Res.2004,37,518.
[4](a)沈宗旋,孔爱娣,陈文勇,张雅文 有机化学,2003,23(1),10;
(b)张占辉,河北师范大学学报(自然科学版),2004,28(6),608;
(c)宓爱巧,楼荣良,蒋耀忠合成化学,1996,4(1),13.
[5]Ooi,A.;Maruoka,K.Angew.Chem.Int.Ed.2007,46,4222.
[6]Ooi,T.;Kameda,M.;Maruoka,K.J.Am.Chem.Soc.1999,121,6519.
[7]For recent reviews,see:
(a)Denissoval,I.;Barriault,L.Tetrahedron 2003,59,10105;
(b)Rlant,O.;Hannedouche,J.Org.Biomol.Chem.2007,5,873;
(c)Kaoru F.Chem.Rev.1993,93,2037.
[8]For recent reviews,see:
(a)Molt,O.;Schrader,T.Synthesis 2002,2633;
(b)Chelucci,G.;Orru,G.;Pinna,G.A.;Tetrahedron 2003,59,9471;
(c)Tang,W.;Zang,X.Chem.Rev.2003,103,3029.
[9]For recent reviews,see:
(a)Mellah,M.;Voituriez,A.;Schulz,E.Chem.Rev.2007,107,5133;
(b)Allenmark,S.Chirality 2008,20,544.
[10]Le Bel Compt.Rend.1891,112,724.
[11]Marckwald,von Droste-Huelshoff Ber.1899,32,560
[12]Wedekind Ber.1899,32,517.
[13]Kauffman,G.B.J.Chem.Educ.1972.49.813.
[14]Vsn't Hoff.J.H.MaondbloduoorNotuunuefansehopppn 1877,7,1W:Ansi-chtonirber die orgonimhs Chomio;Vimeg:Braunschwek,1876,80.
[15](a)Wilkerdt,C.J.Prokf.Chrm.1888,(2)37,449;
(b)1890,(2)41,291.
[16](a)Werner,A.Z.anorg.Chem.1893,3,267;
(b)translated into English with commentary as “Contribution to the Constitution of Inorganic Compounds” in Kanuffman,G.B.Classics in Coordinofion Chemlafrv.Part 1: The Selected Papers of Alfred Werner: New York, 1966: pp 9-88.
[17]Kauffman, G.B.Naturwiss.1976, 63, 324.
[18]Pope, W.J.; Peachey, S.J.J.Chem.Soc.1899,1127.
[19](a) Jones, H.0.J.Chem.Soc.1904, 85, 223; (b) Thomas, M.B.; Jones, H.0.J.Chem.Soc.1906, 89, 280; (c) Jones, H.O.; Hill, J.R.J.Chem.Soc.1908, 93,295; (d) Wedckind, E.; Frohlich, E.Ber.1905,36,3438; 1907,40,1001; (e)Frohlich, E., Wedekind.E.Ber.1907,40,1646; (f) Wedekind, B.; Wedekind, O.Ber.1907, 40, 4450; (g) Wedekind, E.; Mayer, W.Ber.1909.42.303; (h)Everatt,R.W.7.Chem.Soc.1908, 93,1225.
[20](a) Mills, W.H.; Warren, E.H./.Chem.Soc.1925.127, 2507; (b) Mills, W.H.;Bains, L.J.Chem.Soc.1925,127, 2502.
[21]Wyckoff, W.G.; Pasnjek.E.J.Am.Chem.Sor.1921.43.2292; reprinted with annotations in Kauffman, G.B.Classics in Coordimtion Chemistry, Part 3:Twentieth- Century Papers (1904-1935): Dover: New York.1978: pp 89-111.
[22]Recently, the absolute configuration was determined by a single crystal X-ray diffraction, see: Torbeev, V.Y.; Lyssenko, K.A.; Kharybin, O.N.; Antipin, M.Y.; Kostyanovsky, R.G.J.Phys.Chem.B 2003,107,13523.
[23]Kacprzak, K.; Gawronski, J.Synthesis 2001, 961.
[24]Dolling, U.-H.; Davis, P.and Grabowski, E.J.J.J.Am.Chem.Soc.1984,106,446.
[25]O'Donnell, M.J.; Wu, S.; Huffman, J.C.Tetrahedron, 1994,50,4507.
[26]Lygo, B.; Wainwright, P.G Tetrahedron Lett.1997, 38, 8595.
[27]Corey, E.J.; Xu, F.; Noe, M.C.J.Am.Chem.Soc, 1997,119,12414.
[28]Lygo, B.; Crosby , J.; Lowdon, T.R.; Wainwright, P.G.Tetrahedron 200157, 2391.
[29]Chinchilla, R.; Mazon, P.; Nojera, C.Tetrahedron: Asymmetry 2002,13, 927.
[30]Park, H.G; Jeong, B.S.; Yoo, M.S.et al.Tetrahedron Lett.2001,42, 4645.
[31]Thierry, B.; Plaquevent, J.C; Cahard, D.Tetrahedron .Asymmetry 2001,12,983.
[32](a)Von Matus,R.;Kreh,M.;M(u|¨)ller,U.Helv.Chim.Acta.1994,77,1611;
(b)Eddine,J.J.;Cherqaoui,M.Tetrahedron:Asymmetry 1995,6,1225.
[33]Dehmlow,E.V.;Klauck,R.;Duttmann,S.;Neumann,B.;Stammler,H.-G.Tetrahedron:Asymmetry 1998,9,2235.
[34]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[35]Hill,D.A.;Turner,G.L.1992,US 5453510
[36]Kowtoniuk,W.E.;MacFarland,D.K.;Grover,G.N.Tetrahedron Lett.2005,465703.
[37]Kuma,S.;Sobhi,M.E.;Ramachandran,U.Tetrahedron:Asymmetry 2005,16,2599.
[38]潘英明,唐莅东,王恒山等,有机化学,2006,26,3,349。
[39](a)Diego-Castro,M.J.;Hailes,H.C.Chem.Commun.,1998,1549;
(b)Diego-Castro,M.J.,Hailes,H.C.;Lawrence,M.J.Journal of Colloid and Interface Science 2001,234,122.
[40]Gmouh,S.;Jamal-Eddine,J.;Valnot,J.Y.Tetrahedron 2000,56,8361.
[41]王玉成,陈玉芳,顾 菲,辜顺林 中国新药杂志,2007,19,1599.
[42]Starks,C.M.J.Am.Chem.Soc.1971,93,195.
[43](a)Makosza,M.Pure Appl.Chem.1975,43,439;
(b)Yang,H.-M.;Wu,H.S.Catal.Rev.2003,45,463.
[44]Esikova,I.A.;Nahreini,T.S.;O'Donnell,M.J.in Phase-Transfer Catalysis(Ed.:M.E.Halpern),American Chemical Society,Washington,DC,1997,chap.7(ACS Symposium Series 659);
(d)O'Donnell,M.J.;Esikova,I.A.;Shullenberger,D.F.;S.Wu in Phase-Transfer Catalysis(Ed.:M.E.Halpern),American Chemical Society,Washington,DC,1997,chap.10(ACS Symposium Series 659).
[45]Zheng,Z.G.;Wu,T.H;Zheng,R.W.et al Cata.Commu.2007,8,39.
[46]Wang,W.;Buchholz,A.;Ivanova,I.I.et al Chem.Commu.2003,2600;
(b)Wang,W.;Seiler,M.;Ivanova,I.I.;Sternberg,U.et al J.Am.Chem.Soc.2002,124,7548.
[47]Pleiss,U.;Voges,R.Synthesis and Applications of Isotopically Labelled Compounds, eds.Vol.7, Wiley, New York, 2001, pp.1-728.
[48]Ropponen, J.; Lahtinen,M.; Busi,S.; Nissinen, M.; Kolehmainen, E.; Rissanen, K.New J.Chem.2004, 28,1426.
[49]Sommer, H.Z.; Lipp, H.I.; Jackson, L.L.J.Org.Chem.1971,36,824.
[50]Scarpi, D.; Occhiato, E.G.; Guarna, A.J.Org.Chem.1999,64, 1727.
[51]Smith, P.S.; Tan, H.H.J.Org.Chem.1967,32, 2586.
[52]Glaeske, K.W.; West, F.G.Org.Lett.1999,1,31.
[53]Tayama,E.; Tanaka, H.; Nakai, T.Heterocycles, 2005, 66, 95.
[54]Tayama,E.; Nanbara, S.; Nakai, T.Chem.Lett.2006, 35, 478.
[55]Sasai,H.Jpn.Kokai Tokkyo Koho JP 2006076911.
[56]Hirnschall, M.; Treu, M.; Mereiter, K.; Jordis, U.et al.Tetrahedron: Asymmetry 2003, 14, 675.
[57]Hill, R.K.; Chan, T.-K.J.Am.Chem.Soc.1966, 88, 866.
[58]For an example of transfer of biphenyl dissymmetry to asymmetric carbon in the Stevens rearrangement, see (a) Wittig, G.; Zimmermann, H.Chem.Ber.1953, 86,629; (b) Mislow, K.; Joshua, H.J.Am.Chem.Soc.1965, 87, 666.
[59]Eddine, J.J.; Cherqaoui, M.Tetrahedron: Asymmetry 1995, 6,1225.
[60]Arbore, A.P.A.; Cane-Honeysett, D.J.; Coldham, I.; Middleton, M.L.Synlett.2000, 236.
[61](a) Dehmlow, E.V.; Lissel, M.; Heider, J.Tetrahedron 1977, 33, 363; (b) Dehmlow, E.V.; Singh, P.; Heider, J.J.Chem.Res.(S) 1981, 292; (c) Dehmlow, E.V.; Sleegers, A.J.Org.Chem.1988, 53, 3875.
[1](a)Shioiri,T.in Handbook of Phase-Transfer Catalysis(Eds.:Y.Sasson,R.Neumann),Blackie Academic & Professional,London,1997,chap.14;
(b)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1998,4,5;
(c)O'Donnell,M.J.Phases-The Sachem Phase Transfer Catalysis Review 1999, 5,5;
(d)Nelson,A.Angew.Chem.1999 111,1685;Angew.Chem.Int.Ed.1999,38,1583;
(e)Shioiri,T.;Arai,S.in Stimulating Concepts in Chemistry(Eds.:Vogtle,F.;Stoddart,J.F.;Shibasaki,M.),Wiley-VCH,Weinheim,2000,p.123;
(f)O'Donnell,M.J.in Catalytic Asymmetric Syntheses,2nd ed.(Ed.:I.Ojima),Wiley-VCH,New York,2000,chap.10;
(g)M.J.OEDonnell,Aldrichimica Acta 2001,34,3;
(h)Maruoka,K.;Ooi,T.Chem.Rev.2003.103,3013.
(i)O'Donnell,M.J.Acc.Chem.Res.2004,37,506;
(j)Lygo,B.;Andrews,B.I.Acc.Chem.Res.2004,37,518.
[2](a)沈宗旋,孔爱娣,陈文勇,张雅文 有机化学 2003,23(1),10;
(b)张占辉,河北师范大学学报(自然科学版)2004,28(6),608;
(c)宓爱巧,楼荣良,蒋耀忠 合成化学 1996,4(1),13。
[3]Ooi,A.;Maruoka,K.Angew.Chem.Int.Ed.2007,46,4222.
[4]O'Donnell,M.J.;Wu,S.;Huffman,J.C.Tetrahedron 1994,50,4507.
[5]Dehmlow,E.V.;Klauck,R.;Duttmann,S.;Neumann,B.;Stammler,H.-G.Tetrahedron:Asymmetry 1998,9,2235.
[6]von Matusch,R.;Kreh,M.;M(u|¨)ller,U.Helv.Chim.Acta.1994,77,1611.
[7]Hirnschall,M.;Treu,M.;Mereiter,K.;Jordis,U.et al.Tetrahedron:Asymmetry 2003,14,675。
[8]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[9]Pope,W.J.;Peachey,S.J.J.Chem.Soc.1899,1127.
[10]徐春霞,中科院成都生物所硕士学位论文,2005.
[11]李建军,倪爱武,伍新燕,等.科学通报 2002,47(11),837.
[12]Toda,F.;Tanaka,K.;Stein,Z.;Goldberg,I.J.Org.Chem.1994,59,5748.
[13]Wang,Y.;Sun,J.;Ding.K.L.Tetrahedron,2000,56,4447.
[14]umio Toda,Kazuhiro Yoshizawa,Shunji Hyoda,Shinji Toyota,Spyros Chatziefthimiou and Irene M.Mavridis.Organic & Biomolecular Chemistry.2004,2,449.
[15]Ha,W.Z.;Shan,.Z.X.Tetrahedron:Asymmetry 2006,17,854.
[16]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[17]Caira M.R..;Nassimbeni,L.R.,Toda,F.;Vujovic,D.J.Am.Chem.Soc.2000,122,9367.
[18]The Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as deposition No.CCDC-689671(the complex of(NR)-38 and(5)-BINOL),No.CCDC-689672(the complex of(NR)-21 and(S)-BINOL),No.CCDC-689673((NR)-32),No.CCDC-689674((NS)-30),No.CCDC-689675((NR)-39),No.689788(the complex of (NR)-37 and(S)-BINOL),No.CCDC-689789((NR)-33),No.CCDC-689790((NS)-32)and No.CCDC-689791((NS)-34).Copies of the data can be obtained,free of charge,on application to CCDC,12 Union Road,Cambridge CB21EZ,UK[fax:+44(0)4223-336033 or e-mail:deposit@ccdc.cam.ac.uk].
[1]Stohr,C.Bucherschau 1878,477.
[2]Stanger,K.J.;Lee,J.J.;Smith,B.D.J.Org.Chem.2007,72,9663.
[3](a)Sun,H.R.;DiMagno,S.G.Journal of Fluorine Chemistry 2007,128,806;
(b)Baxter,S.J.;Donald B,J.H.;Samuel,C.J.Tetrahedron Letter 1996,37,4617
[4](a)Hofmann,A.W.Ann.1 1851,78,253;
(b)Hofmann,A.W.Ann.1 1851,79,11
[5](a)Hofmann,A.W.Ber.1881,14,659;
(b)Hofmann,A.W.Ber.1881,14,494
[6]Stevens,T.S.;Creighton,E.M.;Gordon,A.B.J.CHEM.Soc.,Aabstracts 1928,3193
[7]Sommelet,M.Compt.Rent.1937,205,56.
[8](a)Bransen,W.R.;Hauser,C.R.Org.Syn.Coll Vol.Ⅳ.1963,508;
(b)Kametani,T.;Kigasawa,K.;Hiiragi,M.;Wagatsuma,N.;Wakisaka,K.Tetrahedron Lett..1969,10,635;
(c)Reich,H.J.;Cohen,M.L.J.Org.Chem.1979,44,3148.
(d)Nicola,M.H.;John,R.M.,Craig R.S.Tetrahedron 1998,54,10899.
(e)Scarpi,D.;Occhiato,E.G.;Guarna,A.J.Org.Chem.1979,44,3148.
[9]Browster,J.B.;Eliel,E.L.In Organic Reactions,Vol.Ⅶ,Roger Adams ed.,John Wiley and Bonn,W.Y.,1853,p.142.
[10]S.Hunig mud W.Baron,Chem.Ber.1957,90,395;1957,90,403.
[11]Glaeske,K.W.;West,F.G.Org.Lett.1999,1,31.
[12]Lygo,B.;Allbutt,B.Synlett 2004,326.
[13]Arai,S.;Tokumaru,T.;Aoyama,T.Tetrahedron lett.2004,45,184
[14]Ooi,T.;Kato,D.;Inamura,K.;Ohmatsu,K.;Maruoka,K.Org.Lett.2007,9,3945
[15]Dehmlow,E.V.;D(u|¨)ttmann,S.;Neumann,B.;Stammler,H.-G.Eur.J.Org.Chem.2002,2087.
[16]Zhang,F.-Y.;Coroy,E.J.Org.Lett.2000,2,1097.
[17]Le Bel Compt.Rend.1891,112,724.
[18]Marckwald,von Droste-Huelshoff Ber.1899,32,560
[19]Tayama,E;Tanaka,H.Tetrahedron Lett.2007,48,4183.
[20]Antoni,G.;Langstrom,B.Journal of Labelled Compounds and Radio-phannaceuticals.1986,XXIV(2),125.