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

Caroline D Evans; Mary F Mahon; Philip C Andrews; James Muir; Steven D Bull

doi:10.1021/ol202750u

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

Caroline D Evans, Mary F Mahon, Philip C Andrews, James Muir, Steven D Bull

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

23 Citations (SciVal)

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.

Original language	English
Pages (from-to)	6276-6279
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	23
DOIs	https://doi.org/10.1021/ol202750u
Publication status	Published - 2 Dec 2011

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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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AU - Evans, Caroline D

AU - Mahon, Mary F

AU - Andrews, Philip C

AU - Muir, James

AU - Bull, Steven D

PY - 2011/12/2

Y1 - 2011/12/2

N2 - 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.

AB - 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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UR - http://dx.doi.org/10.1021/ol202750u

U2 - 10.1021/ol202750u

DO - 10.1021/ol202750u

M3 - Article

SN - 1523-7060

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EP - 6279

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

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

Abstract

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