Electrophilic amination of amino acids with N-boc-oxaziridines: Efficient preparation of N-orthogonally diprotected hydrazino acids and piperazic acid derivatives

JC Hannachi, J Vidal, JC Mulatier…

Index: Vidal, Joelle; Damestoy, Stephanie; Guy, Laure; Hannachi, Jean-Christophe; Aubry, Andre; Collet, Andre Chemistry - A European Journal, 1997 , vol. 3, # 10 p. 1691 - 1709

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Citation Number: 41

Abstract

A general two-step preparation of enantiopure Nα, Nβ-orthogonally diprotected α-hydrazino acids 1 is developed on a multigram scale. The key reaction is the efficient electrophilic amination of N-benzyl amino acids 6 with N-Boc-oxaziridine 7 and accommodates various functional groups encountered in side chains of amino acids. The cyclic 2, 3, 4, 5-tetrahydro- 3-pyridazine carboxylic acid (piperazic acid) derivatives 2 and 3 or the cyclic 3, 4-dihydro- ...