New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted γ-lactams:: Synthesis of the tricyclic core of (±)-martinellines

被引：76
|
作者：
Comesse, Sebastien [1 ]
Sanselme, Morgane [2 ]
Daich, Adam [1 ]
机构：
[1] Univ Havre, UFR Sci & Tech, URCOM, EA 3221, F-76058 Le Havre, France
[2] Univ Rouen, UPRES EA, IRCOF 3233, F-76821 Mont St Aignan, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 14期
关键词：
D O I：
10.1021/jo702752w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of martinelline alkaloids is also described.
引用
收藏
页码：5566 / 5569
页数：4
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