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.
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页码：5605 / 5606
页数：2
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