Intramolecular Ester Enolate–Imine Cyclization Reactions for the Asymmetric Synthesis of Polycyclic β-Lactams and Cyclic β-Amino Acid Derivatives

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

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Bibliographic Details
Published in:Organic letters 2011-12, Vol.13 (23), p.6276-6279
Main Authors: Evans, Caroline D, Mahon, Mary F, Andrews, Philip C, Muir, James, Bull, Steven D
Format: Article
Language:English
Subjects:
Amino Acids, Cyclic - chemical synthesis
Amino Acids, Cyclic - chemistry
beta-Lactams - chemical synthesis
beta-Lactams - chemistry
Combinatorial Chemistry Techniques
Cyclization
Esters
Imines - chemistry
Molecular Structure
Stereoisomerism
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Summary:Enolates of chiral N-(α-methyl-p-methoxybenzyl)-ω-imino-esters undergo intramolecular cyclization reactions to afford (syn)-aza-anions of β-amino esters in high dr that cyclize to afford N-(α-methyl-p-methoxybenzyl)-β-lactams that can be readily deprotected to afford their corresponding cyclic NH-β-lactams, β-amino esters, or β-amino acids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202750u