Journal
ORGANIC LETTERS
Volume 6, Issue 21, Pages 3675-3678Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol048771l
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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.
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