Intramolecular ester enolate–imine cyclization reactions for the asymmetric synthesis of polycyclic β-lactams and cyclic β-amino acid derivatives

Reference:

Evans, C. D., Mahon, M. F., Andrews, P. C., Muir, J. and Bull, S. D., 2011. Intramolecular ester enolate–imine cyclization reactions for the asymmetric synthesis of polycyclic β-lactams and cyclic β-amino acid derivatives. Organic Letters, 13 (23), pp. 6276-6279.

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Official URL:

http://dx.doi.org/10.1021/ol202750u

Abstract

Enolates of chiral N-(alpha-methyl-p-methoxybenzyl)-omega-imino-esters undergo intramolecular cyclization reactions to afford (syn)-aza-anions of beta-amino esters in high dr that cyclize to afford N-(alpha-methyl-p-methoxybenzyl)-beta-lactams that can be readily deprotected to afford their corresponding cyclic NH-beta-lactams, beta-amino esters, or beta-amino acids.

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