Controlling the regioselectivity of lithiation using kinetic isotope effects: Deuterium as a protecting group for carbon

被引：45

作者：

Clayden, J

Pink, JH

Westlund, N

Wilson, FX

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Roche Prod Ltd, Welwyn Garden City AL7 3AY, Herts, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(98)01930-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By substituting deuterium for hydrogen at positions of high kinetic acidity in amides and carbamates, the usual regiochemical course of their reactions with alkyllithiums (ortholithiation vs. lateral lithiation vs. nucleophilic addition) can be altered or overturned by the kinetic isotope effect. The deuterium substituent functions in these reactions as a protecting group for carbon. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：8377 / 8380

页数：4

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