Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow-226001, UP, India.
Chem Asian J. 2011 Jan 3;6(1):189-97. doi: 10.1002/asia.201000554.
An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF(3)·OEt(2))-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin.
本文描述了一种从基于氨基酸的氮丙啶出发高效合成顺式-2,5-二取代手性哌嗪的四步合成策略。该策略的关键步骤是三氟化硼乙醚（BF(3)·OEt(2)）介导的低反应性 N-Ts 手性氮丙啶的高区域选择性开环，随后进行 Mitsunobu 环化，由α-氨基酸甲酯盐酸盐进行。该方案已用于尝试构建天然产物（+）-哌嗪霉素的哌嗪核心骨架。
