Trapping highly reactive dipolarophiles.: Exploiting the mechanism associated with the azomethine ylide strategy for β-lactam synthesis

被引：16

作者：

Brown, GA

Anderson, KM

Large, JM

Planchenault, D

Urban, D

Hales, NJ

Gallagher, T

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 16期

关键词：

D O I：

10.1039/b103271m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly reactive thioaldehydes 7, which are generated transiently by thermolysis of thiosulfinates 6, are trapped using azomethine ylide (derived from the beta -lactam based oxazolidinone 1) to give 2-substituted penams 8. Diethyl thioxomalonate 10 and the selenoxo analogue 13, both of which are generated transiently via a retro Diels-Alder reaction, undergo 1,3-dipolar cycloaddition reactions with 1 to give the isomeric penam 11a and isopenam 11b, and the 2,2-disubstituted selenapenam 14 respectively.

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收藏

页码：1897 / 1900

页数：4

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