Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst

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

Research output: Contribution to journalArticle

Abstract

We provide proof-of-principle that an ambidextrous catalyst is capable of independent, dial-in control of the absolute stereochemistry of two similar nitrostyrene Michael addition reactions by in situ oxidation and reduction of the catalyst. The catalyst is capable of both static and dynamic catalysis modes; in combination both modes allow access to all four possible stereochemical outcomes for the two nitroalkane products in a single process.

Original languageEnglish (US)
Pages (from-to)459-462
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number4
DOIs
StatePublished - Jan 27 2016

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Keywords

  • Ambidextrous
  • Asymmetric catalysis
  • Dynamic
  • Helical inversion
  • Michael addition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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