Inversion of stereochemistry in the Co-2(CO)(8)-catalyzed carbonylation of aziridines to beta-lactams. The first synthesis of highly strained trans-bicyclic beta-lactams

被引:86
作者
Piotti, ME [1 ]
Alper, H [1 ]
机构
[1] UNIV OTTAWA,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA
关键词
D O I
10.1021/ja9531586
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
beta-Lactams were synthesized by the carbonylative ring expansion of aziridines catalyzed by dicobalt octacarbonyl under CO pressure. The active catalyst, cobalt tetracarbonyl anion, induces nucleophilic ring opening of the heterocycle, resulting in inversion of configuration. The regio- and stereospecificity of this reaction resulted in the synthesis of the first highly strained trans-7-azabicyclo[4-2-0]octan-8-one derivatives.
引用
收藏
页码:111 / 116
页数:6
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