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
收藏
页码：11632 / 11640
页数：9
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