title: Regioselective ring-opening of amino acid-derived chiral aziridines: an easy access to cis-2,5-disubstituted chiral piperazines.
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.
authors.affiliation: Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow-226001, UP, India.
authors.forename: Krishnananda
authors.initials: K
authors.lastname: Samanta
authors.forename: Gautam
authors.initials: G
authors.lastname: Panda
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D010879:Piperazines; C036273:piperazinomycin