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Open Access Publications from the University of California

Tandem rhodium catalysis: Exploiting sulfoxides for asymmetric transition-metal catalysis

  • Author(s): Kou, KGM
  • Dong, VM
  • et al.

© The Royal Society of Chemistry. Sulfoxides are uncommon substrates for transition-metal catalysis due to their propensity to inhibit catalyst turnover. In a collaborative effort with Ken Houk, we developed the first dynamic kinetic resolution (DKR) of allylic sulfoxides using asymmetric rhodium-catalyzed hydrogenation. A detailed mechanistic analysis of this transformation using both experimental and theoretical methods revealed rhodium to be a tandem catalyst that promoted both hydrogenation of the alkene and racemization of the allylic sulfoxide. Using a combination of deuterium labelling and DFT studies, a novel mode of allylic sulfoxide racemization via a Rh(iii)-π-allyl intermediate was identified.

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