Organic Chemistry Portal



Highly Efficient Stereoconservative Amidation and Deamidation of α-Amino Acids

Deepak M. Shendage, Roland Fröhlich and Günter Haufe*

*Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany, Email:

D. M. Shendage, R. Froehlich, G. Haufe, Org. Lett., 2004, 6, 3675-3678.

DOI: 10.1021/ol048771l



A stereoconservative protection and deprotection method of amino and carboxyl groups includes the generation of N-Phthaloyl N'-alkyl secondary amides from N-phthaloyl amino acids by using a mixed anhydride method. These secondary amides have been transformed by thermal rearrangement of the intermediate nitrosoamides to esters with retention of configuration and excellent yields.

see article for more examples

N-Protection of Amino Acids

see article for more examples

N-Deprotection of Amides

see article for more examples

Key Words

amidation, amides, deamidation, esters, tert-butyl carbamates

ID: J54-Y2004-830