An aza-enolate alkylation strategy for the synthesis of alpha-alkyl-delta-amino esters and alpha-alkyl valerolactams

Reference:

Taylor, P. J. M., Bull, S. D. and Andrews, P. C., 2006. An aza-enolate alkylation strategy for the synthesis of alpha-alkyl-delta-amino esters and alpha-alkyl valerolactams. Synlett

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Abstract

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.

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