Electrophilic amination of 2-azadienes

被引：38

作者：

Gouverneur, V ^{[1
]}

Ghosez, L ^{[1
]}

机构：

[1] UNIV CATHOLIQUE LOUVAIN,LAB CHIM ORGAN SYNTH,B-1348 LOUVAIN,BELGIUM

来源：

TETRAHEDRON | 1996年 / 52卷 / 21期

关键词：

electrophilic amination; Diels-Alder reaction; nitroso compound; 2-azadiene; alpha-amino acid;

D O I：

10.1016/0040-4020(96)00268-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Azadienes 1 bearing a trialkylsilyloxy group on position 3 can be regarded as carboxylic acid synthons. Their cycloadditions with several classes of nitroso compounds have been studied in details as well as the transformation of the adducts into alpha-amino acids. This study showed that arylnitroso compounds such as nitrosobenzene reacted with 2-azadienes to give adducts that are potential precursors of alpha-N-arylamino acids. We have outlined an important limitation to the use of alpha-chloronitroso compounds. They are not compatible with highly functionalized dienes like 2-azadienes. On the other hand alpha-cyanonitroso and acylnitroso compounds reacted with azadienes to give adducts which were readily converted into alpha-amino acid derivatives. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7585 / 7598

页数：14

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