Stereoselective synthesis of 3,4-trans-disubstituted γ-lactams by cerium(IV) ammonium nitrate mediated radical cyclization of cinnamamides

被引：4

作者：

Nair, Vijay ^{[1
]}

Mohanan, Kishor ^{[1
]}

Suja, Tachapully D. ^{[1
]}

Biju, Akkattu T. ^{[1
]}

机构：

[1] CSIR, Reg Res Lab, Organ Chem Sect, Trivandrum 695019, Kerala, India

来源：

SYNTHESIS-STUTTGART | 2007年 / 08期

关键词：

cerium(IV) ammonium nitrate; intramolecular cyclization; cinnamamides; single electron transfer; gamma-lactams;

D O I：

10.1055/s-2007-965981

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of 3,4-trans-disubstituted gamma-lactams was developed, consisting of the radical cyclization of cinnamamides mediated by cerium(IV) ammonium nitrate. The single-electron-transfer (SET) reaction of the methoxystyrenyl moiety mediated by cerium(IV) ammonium nitrate gives rise to a cation radical, whose cyclization followed by reaction with oxygen and methanol generates 3,4-trans-di substituted gamma-lactams.

引用

页码：1179 / 1184

页数：6

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