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

页码：5566 / 5569

页数：4

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