Highly efficient stereoconservative amidation and deamidation of alpha-amino acids.
[reaction: see text] An overall stereoconservative protection and deprotection method of amino and carboxyl groups is presented. N-Phthaloyl N'-alkyl secondary amides of alpha-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 configuration and excellent yields.
Shendage
Deepak M
DM
Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany.
Fröhlich
Roland
R
Haufe
Günter
G
D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids