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: Hannachi, Jean-Christophe; Vidal, Joelle; Mulatier, Jean-Christophe; Collet, Andre Journal of Organic Chemistry, 2004 , vol. 69, # 7 p. 2367 - 2373

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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- ...