Functionalised bicyclic alcohols by enantioselective α-deprotonation-rearrangement of meso-epoxides

被引：53

作者：

Hodgson, DM ^{[1
]}

Cameron, ID ^{[1
]}

Christlieb, M ^{[1
]}

Green, R ^{[1
]}

Lee, GP ^{[1
]}

Robinson, LA ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 18期

关键词：

D O I：

10.1039/b105369h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective alpha -deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using organolithiums in the presence of (-)-sparteine 3 or (-)-alpha -isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and indolizinol 47 in 50-72% yields and 83-89% ees.

引用

页码：2161 / 2174

页数：14

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