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  • Title: Regioselective ring-opening of amino acid-derived chiral aziridines: an easy access to cis-2,5-disubstituted chiral piperazines.
    Author: Samanta K, Panda G.
    Journal: Chem Asian J; 2011 Jan 03; 6(1):189-97. PubMed ID: 21077094.
    Abstract:
    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.
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