ELECTRONIC EFFECTS ON THE STEREOCHEMICAL OUTCOME OF THE PHOTOCHEMICAL-REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES TO FORM BETA-LACTAMS

被引:40
作者
DUMAS, S [1 ]
HEGEDUS, LS [1 ]
机构
[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
关键词
D O I
10.1021/jo00096a046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The results of calculations by Cossio and subsequently Sordo showing that stereoselectivity in the ketene-imine cycloaddition to form p-lactams could be determined by ''torquoelectronic'' effects similar to those used to rationalize cyclobutene ring opening reactions were used to rationalize the contrasteric outcome of over 40 chromium carbene complex-derived alkoxyketene-imine reactions. In addition, the high stereoselectivity observed in these reactions with optically active heterocyclic imines and the unusual instability of azapenams were rationalized using similar arguments.
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页码:4967 / 4971
页数:5
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