Chirality transfer from carbon to nitrogen to carbon via cyclic ammonium ylides

被引：83

作者：

Glaeske, KW ^{[1
]}

West, FG ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 01期

关键词：

D O I：

10.1021/ol9905349

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic ammonium salts 2 were prepared by diastereoselective quaternization of nitrogen in the corresponding proline or threonine derivatives. Upon treatment with base, salts 2 underwent [1,2]- or [2,3]-shift to 3 with moderate to complete stereospecificity. The overall process entails chirality transfer from the original alpha carbon to the neighboring nitrogen and then back to the carbon.

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页码：31 / 33

页数：3

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