Free radical-mediated vinyl amination: a mild, general pyrrolidinyl enamine synthesis

被引:34
作者
Nugent, BM [1 ]
Williams, AL [1 ]
Prabhakaran, EN [1 ]
Johnston, JN [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
vinyl amination; free radicals; enamines; alkyne aminostannation; beta-stannyl enamine;
D O I
10.1016/j.tet.2003.04.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The complete scope of free radical-mediated vinyl amination is described, using 5-exo-trig cyclizations of vinyl radicals to the nitrogen of azomethines. The focus is primarily on NN-dialkyl enamines since their nucleophilicity renders them the most challenging enamines to synthesize using redox conditions. These studies establish several encouraging precedents for the broader application of this strategy. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8877 / 8888
页数:12
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