A General and Simple Removal of the Allyloxycarbonyl Protecting Group by Palladium-Catalyzed Reactions Using Nitrogen and Sulfur Nucleophiles

Jean Pierre Genêt; Errol Blart; Monique Savignac; Stéphane Lemeune; Sandrine Lemaire-Audoire; Jean Marie Bernard

doi:10.1055/s-1993-22570

Synlett 1993; 1993(9): 680-682
DOI: 10.1055/s-1993-22570

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A General and Simple Removal of the Allyloxycarbonyl Protecting Group by Palladium-Catalyzed Reactions Using Nitrogen and Sulfur Nucleophiles

Jean Pierre Genêt^* , Errol Blart, Monique Savignac, Stéphane Lemeune, Sandrine Lemaire-Audoire, Jean Marie Bernard

^*Ecole Nationale Supérieure de Chimie de Paris, Laboratoire de Synthèse Organique, Unité 1381 associée au CNRS, 11 rue Pierre et Marie Curie, F-75231 Paris, France

Abstract

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Smooth removal of the Allyloxycarbonyl (Alloc) moiety from allylic esters, carbamates and carbonates is carried out by Pd (O) catalyzed allyl transfer to diethylamine and thio derivatives as the accepting nucleophiles. The method has been successfully used for selective deprotection of secondary amines and base sensitive substrates.

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