Efficient synthesis of quaternary α-hydroxy acids by alkylation of α-ketoamide-derived dienediolates

被引：8
|
作者：
Newton, R [1 ]
Marsden, SP [1 ]
机构：
[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England
来源：
SYNTHESIS-STUTTGART | 2005年 / 19期
关键词：
ketoamides; alkylations; dianions; hydroxy acids; stereoselective olefin synthesis;
D O I：
10.1055/s-2005-918481
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Double deprotonation of alpha-ketoamides generates dienediolates. which Undergo regioselective alpha-alkylation to yield alpha-substituted-alpha-hydroxy-beta,gamma-unsaturated amides. 1,2-Disubstituted alkenes are generated exclusively as the E-isonier. 1,1-Disubstituted and 1.1.2-trisubstituted olefins can also be prepared. The amides can be readily converted to the corresponding acids.
引用
收藏
页码：3263 / 3270
页数：8
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