Shendage Deepak M, Fröhlich Roland, Haufe Günter
Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany.
Org Lett. 2004 Oct 14;6(21):3675-8. doi: 10.1021/ol048771l.
[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.
[反应：见正文] 本文提出了一种氨基和羧基的整体立体保守保护和脱保护方法。α-氨基酸的N-邻苯二甲酰基-N'-烷基仲酰胺可通过使用混合酸酐法使N-烷基胺与相应的N-邻苯二甲酰基氨基酸发生偶联反应生成。这些仲酰胺可通过中间亚硝基酰胺的热重排转化为构型保持且产率优异的O-烷基酯。
