A CONTRIBUTION TO THE CONFUSION SURROUNDING THE REACTION OF KETENES WITH IMINES TO PRODUCE BETA-LACTAMS - A COMPARISON OF STEREOSELECTIVITY DEPENDENCE ON THE METHOD OF KETENE GENERATION - ACID CHLORIDE TRIETHYLAMINE VS PHOTOLYSIS OF CHROMIUM CARBENE COMPLEXES

被引：190

作者：

HEGEDUS, LS

MONTGOMERY, J

NARUKAWA, Y

SNUSTAD, DC

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 15期

关键词：

D O I：

10.1021/ja00015a036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselectivity of the reaction of imines of benzaldehyde and cinnamaldehyde with ketenes generated by the reaction of optically active oxazolidinone acid chlorides with triethylamine and complexed ketenes generated by photolysis of optically active oxazolidine- and oxazolidinone-chromium-carbene complexes in the presence and absence of added triethylamine was compared. The absolute stereochemistry was determined primarily by the structure of the chiral auxiliary. The relative (cis-trans) stereochemistry was determined primarily by the structure of the imine and the free or bound character of the ketene. Triethylamine addition to reactions of carbene complexes afforded results that closely paralleled that of acid chloride generated ketenes. A mechanistic scheme accounting for these results and the general trends observed in other ketene/imine cyclizations is provided.

引用

页码：5784 / 5791

页数：8

共 39 条

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