On the use of deuterium isotope effects in chemical synthesis

被引：31

作者：

Dudley, GB

Danishefsky, SJ

Sukenick, G

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 32期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(02)01114-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The decreased kinetic acidity of deuterium relative to hydrogen can be used to gain an advantage in the reductive cyclization of an alkenyllithium species onto a ketone. The intermediate alkenyllithium can add to the carbonyl or abstract an alpha-proton, giving rise to two products. The yield of the cyclized product can be increased, and the formation of the uncyclized by-product can be suppressed, by replacing the acidic protons with deuterons prior to cyclization. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5605 / 5606

页数：2

共 19 条

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