Asymmetric synthesis of. beta.-amino acids. 1. Highly diastereoselective addition of a racemic. beta.-alanine enolate derivative to electrophiles

…, D Quintana, B Lamatsch, D Seebach

Index: Juaristi, Eusebio; Quintana, Delia; Lamatsch, Bernd; Seebach, Dieter Journal of Organic Chemistry, 1991 , vol. 56, # 7 p. 2553 - 2557

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Citation Number: 84

Abstract

@-Alanine, an inexpensive a-amino acid, was converted into the 2-tert- butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C (2), which directs addition from the enolate ...

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