Abstract
Diastereomerically pure azepane derivatives 5, 13 were prepared by piperidine ring expansion with exclusive stereoselectivity and regioselectivity and in excellent yield. The structure and stereochemistry of 5 were confirmed via X-ray crystallographic analysis. The ring expansion strategy was applied to the construction of an azepine backbone 22 of a potential biologically active compound. The regiochemistry and stereochemistry of the piperidine ring expansion process were investigated by semiempirical molecular orbital calculations.
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