Carbonyl allenylation/free radical cyclization sequence as a new regio- and stereocontrolled access to bi- and tricyclic β-lactams

被引：38

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro

Aragoncillo, Cristina

Redondo, Maria C.

机构：

[1] Univ Complutense Madrid, Dept Quim Organ 1, Fac Quim, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 05期

关键词：

D O I：

10.1021/jo061828s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to racemic and enantiopure nonconventional fused bi- and tricyclic beta-lactams has been developed by using regio- and stereocontrolled intramolecular free radical reactions in monocyclic 2-azetidinone-tethered allenynes and haloallenes. The access to allene cyclization precursors was achieved by metal-mediated carbonyl allenylation of appropriately substituted 4-oxoazetidine-2-carbaldehydes in an aqueous environment. The tin-promoted radical cyclizations of allene-beta-lactams are totally regioselective for the central allenic carbon, providing bi- and tricyclic beta-lactams containing a seven-membered ring.

引用

页码：1604 / 1608

页数：5

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