Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes

被引：76

作者：

Alcaide, B ^{[1
]}

Almendros, P ^{[1
]}

Aragoncillo, C ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 05期

关键词：

D O I：

10.1021/jo005715z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DABCO promoted reactions of various activated vinyl systems with optically pure 4-oxoazetidine-2-carbaldehydes 1 gave rise to Baylis-Hillman adducts 3 With excellent syn stereoselectivities, without detectable racemization. Products 3 are used. for the asymmetric preparation of unusual 2-azetidinones fused to medium-sized rings via chemo- and Stereocontrolled divergent radical cyclization. The formation of bicyclic beta -lactams 4-6 could be rationalized through a tandem radical Michael addition/endo cyclization or a tandem radical addition/Michael addition, depending pn the electronic nature of the radical promoter.

引用

页码：1612 / 1620

页数：9

共 109 条

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