Microwave- and photoirradiation-induced staudinger reactions of cyclic imines and ketenes generated from α-diazoketones.: A further investigation into the stereochemical process

被引：100

作者：

Liang, Y ^{[1
]}

Jiao, L ^{[1
]}

Zhang, SW ^{[1
]}

Xu, JX ^{[1
]}

机构：

[1] Peking Univ, Coll Chem & Mol Engn, Dept Biol Chem, Minist Educ,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 01期

关键词：

D O I：

10.1021/jo048328o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of ketenes generated from alpha-diazoketones with a series of acyclic and cyclic imines were investigated under both microwave and photoirradiation conditions. The results indicate that the zwitterionic azabutadiene-type intermediates yielded from imines and ketenes undergo a conrotatory ring closure exclusively to produce beta-lactams. It is notable that no Woodward-Hoffmann product was found under the ultraviolet irradiation. The photoirradiation-induced Staudinger reaction shows a different stereo selectivity from the electrocyclic reaction of substituted 1,3-butadiene.

引用

页码：334 / 337

页数：4

共 30 条

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