Enantioselective synthesis of beta-amino acids using hexahydrobenzoxazolidinones as chiral auxiliaries

…, E Jiménez-González, JL Olivares-Romero…

Index: Reyes-Rangel, Gloria; Jimenez-Gonzalez, Erika; Olivares-Romero, Jose Luis; Juaristi, Eusebio Tetrahedron Asymmetry, 2008 , vol. 19, # 24 p. 2839 - 2849

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Citation Number: 11

Abstract

A practical synthetic route for the asymmetric synthesis of β2-amino acids is described. In the first step, the procedure involves the N-acylation of readily available, enantiopure hexahydrobenzoxazolidinone (4R, 5R)-1 with 3-methylbutanoyl chloride 2, 4- methylpentanoic acid 3, and 3-(1-tert-butoxycarbonyl)-1H-indol-3-yl) propanoic acid 4 to afford derivatives 5a, 5b, and 5c, respectively, which were alkylated with high ...