Tetrahedron Letters

Biomimetic synthesis of α-amino acids from α-keto acids

S Shinkai, H Hamada, A Dohyama, O Manabe

Index: Shinkai, Seiji; Hamada, Hisatake; Dohyama, Akihiko; Manabe, Osamu Tetrahedron Letters, 1980 , vol. 21, p. 1661 - 1664

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Citation Number: 10

Abstract

Protonated α-imino acids, RC(=NH 2 + )COOH, were easily reduced to α-amino acids by an acid-stable NADH analogue, 1-benzyl-3-carbamoyl-1,4-dihydroquinoline. This is the first model reaction of NADH-mediated α-amino acid synthesis from α-keto acids. ... The authentic sample of N-benzyl-2-picolylamine was prepared by the NaBH 4 reduction of N- (2-picolylidene)benzylamine in absolute ethanol: yield 70%, mp 205–209°C. The structure was confirmed by elemental ...