Abstract

ESCALANTE, Jaime; HERNANDEZ, Ana Lilia  and  JUARISTI, Eusebio. Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles. Rev. Soc. Quím. Méx [online]. 2001, vol.45, n.4, pp.177-182. ISSN 0583-7693.

β-Alanine, an inexpensive β-amino acid, was converted into the 2-phenylperhydropyrimidin-4-one derivative (1), which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of (1)-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the phenyl group at C(2), which directs addition from the enolate face opposite to this group. These results pave the road to the enantioselective synthesis of α-substituted β-amino acids.

Keywords : β-amino acid; diastereoselective alkylation; perhydropyrimidinone.

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