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Regioselective Ring‐Opening of Amino Acid‐Derived Chiral Aziridines: an Easy Access to cis ‐2,5‐Disubstituted Chiral Piperazines
Author(s) -
Samanta Krishnananda,
Panda Gautam
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000554
Subject(s) - regioselectivity , boron trifluoride , ring (chemistry) , chemistry , hydrochloride , amino acid , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry
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.