New catalysts for the base-promoted isomerization of epoxides to allylic alcohols.: Broadened scope and near-perfect asymmetric induction

被引：44

作者：

Bertilsson, SK ^{[1
]}

Södergren, MJ ^{[1
]}

Andersson, PG ^{[1
]}

机构：

[1] Uppsala Univ, Inst Chem, Dept Organ Chem, S-75121 Uppsala, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 05期

关键词：

D O I：

10.1021/jo010934l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl]methyl-2-azabicyclo-[2.2.1]heptanes were evaluated as catalysts for the enantioselective beta-elimination of meso-epoxides. The (2R,5R)-dimethylpyrrolidinyl-substituted catalyst 4 exhibited exceptionally high enantioselectivity and reactivity, and several substrates were rearranged with enantioselectivities of 98-99% ee. In addition, the use of 4 allowed the first successful, true catalytic rearrangement of the difficult substrates cyclopentene oxide (81%, 96% ee) and (Z)-4-octene oxide (80%, 91% ee).

引用

页码：1567 / 1573

页数：7

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