A redox-reconfigurable, ambidextrous asymmetric catalyst

Shahab Mortezaei, Noelle R. Catarineu, James W. Canary

Research output: Contribution to journalArticle

Abstract

A redox-reconfigurable catalyst derived from l-methionine and incorporating catalytic urea groups has been synthesized. This copper complex catalyzes the enantioselective addition of diethyl malonate to trans-β-nitrostyrene. Either enantiomer of the product can be predetermined by selection of the oxidation state of the copper ion. Enantiomeric excesses of up to 72% (S) and 70% (R) were obtained in acetonitrile. The ability of the catalyst to invert enantiomeric preference was reproduced with several different solvents and bases. Facile interconversion between the Cu 2+ and Cu + redox states allowed easy access to both active helical forms of the complex and, therefore, dial-in enantioselectivity.

Original languageEnglish (US)
Pages (from-to)8054-8057
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number19
DOIs
StatePublished - May 16 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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