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| LETTER | Synlett 2006: 1347-1350
DOI: 10.1055/s-2006-939726 |
© Georg Thieme Verlag Stuttgart · New York
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An Aza-Enolate Alkylation Strategy for the Synthesis of α-Alkyl-δ-amino Esters and α-Alkyl Valerolactams
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| Piers J. M. Taylora, Steven D. Bull*a, Philip C. Andrewsb |
a Department of Chemistry, University of Bath, Bath, BA2 7AY, UK
Fax: +44(1225)386231; e-Mail: s.d.bull@bath.ac.uk;
b School of Chemistry, Monash University, P.O. Box 23, Clayton, Melbourne, Vic. 3800, Australia
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Received
13 February 2006 |
Abstract
Alkylation of the aza-enolate of valerolactim methyl ether with electrophiles affords α-alkyl lactims that may be hydrolysed under mild acidic conditions to afford their corresponding α-alkyl-δ-amino esters as their hydrochloride salts. Neutralisation of these salts with base results in smooth intramolecular cyclisation to afford their corresponding α-alkyl lactams in excellent yield. Key words
lactim ether - aza-enolate - alkylation - α-alkyl-δ-amino ester - α-alkyl lactams
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