DBU-promoted condensation of acyldiazomethanes to aldehydes and imines under catalytic conditions

被引:84
作者
Jiang, N [1 ]
Wang, JB [1 ]
机构
[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Dept Biol Chem, Beijing 100871, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(01)02375-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The condensation of acyldiazomethanes to aldehydes and imines can be promoted with catalytic amount of DBU. The condensation gives beta-hydroxy alpha-diazo carbonyl compounds or beta-amino alpha-diazo carbonyl compounds in high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1285 / 1287
页数:3
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