Kinetic resolution of racemic alkoxy oxiranes by chiral lithium amides

被引：17
作者：
Bigi, A
Mordini, A
Thurner, A
Faigl, F
Poli, G
Toke, L
机构：
[1] Dipartimento Chim Organ U Schiff, Ctr CNR Composti Eterocicl, I-50121 Florence, Italy
[2] Tech Univ Budapest, Hungarian Acad Sci, Res Grp, Dept Organ Chem Technol, H-1521 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期
基金：
新加坡国家研究基金会; 匈牙利科学研究基金会;
关键词：
D O I：
10.1016/S0957-4166(98)00239-0
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The isomerization of alkoxy oxiranes with chiral lithium amides has been carefully investigated with the aim of finding an enantioselective approach to hydroxy enolethers, a class of compounds which can be used for further synthetic elaborations. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2293 / 2299
页数：7
相关论文
共 28 条
[1]   CATALYTIC ENANTIOSELECTIVE DEPROTONATION OF MESO-EPOXIDES BY THE USE OF CHIRAL LITHIUM AMIDE [J].
ASAMI, M ;
ISHIZAKI, T ;
INOUE, S .
TETRAHEDRON-ASYMMETRY, 1994, 5 (05) :793-796
[2]   RECONFIRMATION OF HIGH ENANTIOMERIC EXCESSES IN THE ENANTIOSELECTIVE TRANSFORMATION OF MESO-EPOXIDES [J].
ASAMI, M ;
INOUE, S .
TETRAHEDRON, 1995, 51 (43) :11725-11730
[3]   ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO ALLYLIC ALCOHOLS BY LITHIUM (S)-2-(N,N-DISUBSTITUTED AMINOMETHYL)PYRROLIDIDE [J].
ASAMI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (03) :721-727
[4]   AN ASYMMETRIC-SYNTHESIS OF (-)-CARBOVIR [J].
ASAMI, M ;
TAKAHASHI, J ;
INOUE, S .
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1649-1652
[5]   A KINETIC RESOLUTION OF RACEMIC EPOXIDES BY A CHIRAL LITHIUM AMIDE [J].
ASAMI, M ;
KANEMAKI, N .
TETRAHEDRON LETTERS, 1989, 30 (16) :2125-2128
[6]   AN ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO BOTH ENANTIOMERS OF ALLYLIC ALCOHOLS BY CHIRAL LITHIUM AMIDES [J].
ASAMI, M ;
KIRIHARA, H .
CHEMISTRY LETTERS, 1987, (02) :389-392
[7]   AN ASYMMETRIC TRANSFORMATION OF CYCLOHEXENE OXIDE TO (S)-2-CYCLOHEXEN-1-OL BY CHIRAL LITHIUM AMIDES [J].
ASAMI, M .
CHEMISTRY LETTERS, 1984, (05) :829-832
[8]   A short synthesis of (S)-2-(diphenylmethyl)pyrrolidine, a chiral solvating agent for NMR analysis [J].
Bailey, DJ ;
OHagan, D ;
Tavasli, M .
TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :149-153
[9]   Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides [J].
Bhuniya, D ;
DattaGupta, A ;
Singh, VK .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6108-6113
[10]   ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES [J].
CAIN, CM ;
COUSINS, RPC ;
COUMBARIDES, G ;
SIMPKINS, NS .
TETRAHEDRON, 1990, 46 (02) :523-544
123