Synthesis of β-substituted alanines via Michael addition of nucleophiles to dehydroalanine derivatives

被引:36
作者
Ferreira, PMT [1 ]
Maia, HLS [1 ]
Monteiro, LS [1 ]
Sacramento, J [1 ]
Sebastiao, J [1 ]
机构
[1] Univ Minho, Dept Chem, P-4700320 Braga, Portugal
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 19期
关键词
D O I
10.1039/b003353g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several beta-substituted alanines are synthesised in high yields by a Michael addition of nucleophiles to N-acyl-N-(tert-butoxycarbonyl)dehydroalanine methyl ester, using mild reaction conditions and simple work-up procedures. The same method can be applied to dipeptides containing dehydroalanine.
引用
收藏
页码:3317 / 3324
页数:8
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