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 a-alkyl lactims that may be hydrolysed under mild acidic conditions to afford their corresponding alpha-alkyl-8-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.