Stereoselective synthesis and functionalization of N-alkyl-β-lactams

被引：16

作者：

Troisi, Luigino ^{[1
]}

Granito, Catia ^{[1
]}

Pindinelli, Emanuela ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Sci & Tecnol Biol Ambientali, I-73100 Lecce, Italy

来源：

TETRAHEDRON | 2008年 / 64卷 / 51期

关键词：

beta-Lactams; Carbanions; Diastereoselectivity; Functionalization;

D O I：

10.1016/j.tet.2008.10.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel polyfunctionalized N-alkyl-beta-lactams were prepared with high stereoselectivity in an efficient manner by a palladium-catalyzed [2+2] carbonylative cycloaddition of allyl bromide with heteroarylidene N-alkyl-amines The type of alkyl group linked to the nitrogen atom influences the reaction stereoselectivity. Moreover, the C-3 and the C-4 positions of the azetidinone ring can be further stereoselectively functionalized inserting various groups through the generation of a stable azeticlinyl carbanion and then captured by various electrophiles. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：11632 / 11640

页数：9

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