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
收藏
页码：1179 / 1184
页数：6
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