Tetrahedron

Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids

O Muñoz-Muñiz, E Juaristi

Index: Munoz-Muniz, Omar; Juaristi, Eusebio Tetrahedron, 2003 , vol. 59, # 23 p. 4223 - 4229

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Citation Number: 28

Abstract

Achiral 1-benzoyl-3-methylperhydropyrimidin-4-one (1) was deemed a useful, potential precursor for the enantioselective synthesis of α-substituted β-amino acids. Pyrimidinone 1 was prepared from inexpensive β-aminopropanoic acid in 62% overall yield. Prochiral enolate derivative 1-Li was alkylated in good yield and moderate enantioselectivity in the presence of chiral amines (S)-8,(S, S)-9,(S, S)-10, or (−)-sparteine. The enantioselectivity ...