Abstract
The different modes of interaction between achiral ketenes and homochiral aldimines derived from chiral aldehydes to give the two possible diastereoisomers of cis-β-lactams have been examined using the AM 1 method. It has been found that the step which determines the final stereochemistry is the conrotatory ring closure between C 3 and C 4 atoms. The high diastereoselectivity predicted by our calculations is in excellent agreement with available experimental data. The origin of this high stereocontrol is rationalized on the basis of the stabilizing interaction between the C-X a orbital (X being an electronegative atom) and the p atomic orbital of the C 3 atom
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