Novel catalytic kinetic resolution of racemic epoxides to allylic alcohols

被引:38
作者
Gayet, A [1 ]
Bertilsson, S [1 ]
Andersson, PG [1 ]
机构
[1] Uppsala Univ, Inst Chem, Dept Organ Chem, S-75121 Uppsala, Sweden
关键词
D O I
10.1021/ol025983e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the U-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.1] heptane 1 as catalyst allowed both epoxides and allylic alcohols to be obtained in an enantioenriched form.
引用
收藏
页码:3777 / 3779
页数:3
相关论文
共 21 条
[1]   A novel highly effective chiral lithium amide for catalytic enantioselective deprotonation of meso-epoxides [J].
Asami, M ;
Suga, T ;
Honda, K ;
Inoue, S .
TETRAHEDRON LETTERS, 1997, 38 (36) :6425-6428
[2]   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
[3]   A KINETIC RESOLUTION OF RACEMIC EPOXIDES BY A CHIRAL LITHIUM AMIDE [J].
ASAMI, M ;
KANEMAKI, N .
TETRAHEDRON LETTERS, 1989, 30 (16) :2125-2128
[4]   Kinetic resolution of cis-3-alkylcyclohexene oxide by a chiral lithium amide -: An application to a synthesis of both enantiomers of isomenthone [J].
Asami, M ;
Sato, S ;
Honda, K ;
Inoue, S .
HETEROCYCLES, 2000, 52 (03) :1029-+
[5]   Asymmetric transformation of meso-epoxides by chiral lithium amides [J].
Asami, M .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1996, 54 (03) :188-199
[7]   ENANTIOSELECTIVE DEPROTONATION OF CYCLOHEXENE OXIDE TO (R)-2-CYCLOHEXEN-1-OL [J].
BHUNIYA, D ;
SINGH, VK .
SYNTHETIC COMMUNICATIONS, 1994, 24 (10) :1475-1481
[8]   Kinetic resolution of racemic alkoxy oxiranes by chiral lithium amides [J].
Bigi, A ;
Mordini, A ;
Thurner, A ;
Faigl, F ;
Poli, G ;
Toke, L .
TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2293-2299
[9]   ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].
COX, PJ ;
SIMPKINS, NS .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26
[10]   BASE-PROMOTED REACTIONS OF EPOXIDES .V. 1-ALKYLCYCLOALKENE OXIDES [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2375-&