Organic letters

Highly efficient stereoconservative amidation and deamidation of α-amino acids

DM Shendage, R Fröhlich, G Haufe

Index: Shendage, Deepak M.; Froehlich, Roland; Haufe, Guenter Organic Letters, 2004 , vol. 6, # 21 p. 3675 - 3678

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Citation Number: 150

Abstract

An overall stereoconservative protection and deprotection method of amino and carboxyl groups is presented. N-Phthaloyl N'-alkyl secondary amides of α-amino acids can be generated from corresponding N-phthaloyl amino acids by coupling reaction of N- alkylamines using mixed anhydride method. These secondary amides can be transformed by thermal rearrangement of intermediate nitrosoamides to O-alkyl esters with retention of ...

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