Structurally novel Bi- and tricyclic β-lactams via [2+2] cycloaddition or radical reactions in 2-azetidinone-tethered enallenes and allenynes

被引：55

作者：

Alcaide, B ^{[1
]}

Almendros, P

Aragoncillo, C

机构：

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

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

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol034995c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Thermolysis of beta-lactam-tethered enallenyl alcohols gave tricyclic ring structures via a formal [2 + 2] cycloaddition of the alkene with the distal bond of the allene, while the tin-promoted radical cyclization in 2-azetidinone-tethered allenynes proceeded to provide bicyclic beta-lactams containing a medium-sized ring. The access to cyclization precursors was achieved by regio- and stereoselective metal-mediated carbonyl allenylation of 4-oxoazetidine-2-carbaldehydes in an aqueous environment.

引用

页码：3795 / 3798

页数：4

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