Enantioselective rearrangement of exo-norbornene oxide to nortricyclanol

被引：22

作者：

Hodgson, DM ^{[1
]}

Wisedale, R ^{[1
]}

机构：

[1] UNIV READING,DEPT CHEM,READING RG6 2AD,BERKS,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 05期

关键词：

D O I：

10.1016/0957-4166(96)00142-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective alpha-deprotonation-rearrangement of exo-norbornene oxide 1 to (-)-nortricyclanol 2 in up to 52% ee using a nonracemic lithium amide, or an organolithium in the presence of (-)-sparteine, is described. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1275 / 1276

页数：2

共 7 条

[1] AN ENHANCEMENT OF ENANTIOSELECTIVITY IN CHIRAL LITHIUM AMIDE DEPROTONATIONS DUE TO LITHIUM-CHLORIDE
BUNN, BJ
SIMPKINS, NS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) : 533 - 534
[2] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES
COX, PJ
SIMPKINS, NS
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (01) : 1 - 26
[3] CRANDALL JK, 1983, ORG REACTIONS, V29, P345
[4] REARRANGEMENTS OF NORBORNENCE OXIDE
CRANDALL, JK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) : 2830 - &
[5] ABSOLUTE-CONFIGURATION OF OPTICALLY-ACTIVE TRICYCLO[2.2.1.02,6]HEPTAN-3-O1 (NORTRICYCLANOL) - AN ENHANCEMENT OF ENANTIOMERIC PURITY OF A CHIRAL ALCOHOL BY REPEATING ENZYMATIC KINETIC RESOLUTION
HIROSE, Y
ANZAI, M
SAITOH, M
NAEMURA, K
CHIKAMATSU, H
[J]. CHEMISTRY LETTERS, 1989, (11) : 1939 - 1942
[6] Highly enantioselective rearrangement of quaternary carbon-containing meso-epoxides to allylic alcohols
Hodgson, DM
Gibbs, AR
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (02) : 407 - 408
[7] HODGSON DM, 1996, J CHEM SOC CHEM COMM, P1015

← 1 →