139712-95-1Relevant academic research and scientific papers
Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines
Samanta, Krishnananda,Panda, Gautam
, p. 189 - 197 (2011)
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 (BF3·OEt2)-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. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright
