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Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one (derived from l-valine) and alkylation of the resultant lithium beta-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)-N(3)-(2'-alkylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnishes a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yield and high ee. Additionally, the boron-mediated aldol reaction of beta-amino N-acyl oxazolidinones is a highly diastereoselective method for the synthesis of a range of beta-amino-beta'-hydroxy N-acyl oxazolidinones.

Original publication

DOI

10.1039/b707689d

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/09/2007

Volume

5

Pages

2812 - 2825

Keywords

Alkylation, Amides, Amino Acids, Crystallography, X-Ray, Imaging, Three-Dimensional, Lithium, Models, Molecular, Molecular Structure, Oxazoles, Protons, Stereoisomerism, beta-Alanine