Liebigs Annalen

On the preparation of β??amino acids from α??amino acids using the Arndt??Eistert reaction: Scope, limitations and stereoselectivity. Application to carbohydrate …

J Podlech, D Seebach

Index: Podlech, Joachim; Seebach, Dieter Liebigs Annalen, 1995 , # 7 p. 1217 - 1228

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Citation Number: 84

Abstract

Abstract The Arndt-Eistert homologation of α-amino acids was studied to determine the stereoselectivity in this reaction by chromatographic up-to-date analytical methods. While carba-mate-protected phenylglycine was transformed to the corresponding β-amino acid methyl ester with a stereoselectivity of only 9: 1, all other tested amino acid derivatives (Ala, Phe, Ser, Orn, tert-Leu and perhydro-azepine-2-carboxylic acid, suitably protected) were ...