An Aza-Enolate Alkylation Strategy for the Synthesis of (alpha)-Alkyl-(delta)-amino Esters and (alpha)-Alkyl Valerolactams

Alkylation of the aza-enolate of valerolactim methyl ether with electrophiles affords (alpha)-alkyl lactims that may be hydro­lysed under mild acidic conditions to afford their corresponding (alpha)-alkyl-(delta)-amino esters as their hydrochloride salts. Neutralisation of these salts with base results in smooth intramolecular cyclisation to afford their corresponding (alpha)-alkyl lactams in excellent yield.