Palladium-catalyzed transprotection of allyloxycarbonyl-protected amines: efficient one-pot formation of amides and dipeptides

…, P Bernabe, H Hiemstra, WN Speckamp…

Index: Roos; Bernabe; Hiemstra; Speckamp; Kaptein; Boesten Journal of Organic Chemistry, 1995 , vol. 60, # 6 p. 1733 - 1740

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Citation Number: 51

Abstract

The synthetic utility of the N4allyloxycarbonyl)(Alloc) substituent in a-amino acid derivatives is substantially extended beyond its well-known function as an amine protecting group. When the palladium-catalyzed deprotection is carried out by using tributyltin hydride as nucleophile (the Guibe method) in the presence of an active acylating agent a new acyl group is introduced on nitrogen. Successful acylating agents include carboxylic acid ...