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Issue 21, 2015
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Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis

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Abstract

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.

Graphical abstract: Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis

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Publication details

The article was received on 15 Jan 2015, accepted on 15 Apr 2015 and first published on 05 May 2015


Article type: Perspective
DOI: 10.1039/C5OB00083A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 5844-5847
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    Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis

    K. G. M. Kou and V. M. Dong, Org. Biomol. Chem., 2015, 13, 5844
    DOI: 10.1039/C5OB00083A

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