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Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary alpha-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis.

Original publication

DOI

10.1039/b704475e

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/07/2007

Volume

5

Pages

2138 - 2147

Keywords

Alkylation, Amino Acids, Crystallography, X-Ray, Diketopiperazines, Hydrolysis, Lactams, Methylation, Models, Molecular, Molecular Structure, Piperazines, Protons, Stereoisomerism