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An Aza-Enolate Alkylation Strategy for the Synthesis of α-Alkyl-δ-amino Esters and α-Alkyl Valerolactams

Piers J. M. Taylor, Steven D. Bull*, Philip C. Andrews

*Department of Chemistry, University of Bath, Bath, BA2 7AY, UK, Email:

P. J. M. Taylor, S. D. Bull, P. C. Andrews, Synlett, 2006, 1347-1350.

DOI: 10.1055/s-2006-939726

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Alkylation of the aza-enolate of valerolactim methyl ether with electrophiles affords α-alkyl lactims. Subsequent mild, acidic hydrolysation gives the corresponding α-alkyl-δ-amino esters hydrochloride salts. Neutralisation of these salts with base results in smooth intramolecular cyclisation to afford α-alkyl lactams in excellent yield.

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Key Words

lactim ethers, aza-enolates, alkylation, α-alkyl-δ-amino ester, α-alkyl lactams

ID: J60-Y2006-4410