381223-76-3Relevant articles and documents
Stereoselective and regioselective synthesis of azepane and azepine derivatives via piperidine ring expansion
Chong, Hyun-Soon,Ganguly, Bishwajit,Broker, Grant A.,Rogers, Robin D.,Brechbiel, Martin W.
, p. 2080 - 2086 (2002)
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.