Regioselective ring-opening of amino acid-derived chiral aziridines: an easy access to cis-2,5-disubstituted chiral piperazines

Chem Asian J. 2011 Jan 3;6(1):189-97. doi: 10.1002/asia.201000554.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aziridines / chemistry*
  • Molecular Structure
  • Piperazines / chemistry*
  • Stereoisomerism

Substances

  • Aziridines
  • Piperazines
  • piperazinomycin