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Org Lett. 2013 Mar 1;15(5):1148-51. doi: 10.1021/ol400363f. Epub 2013 Feb 20.

Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents.

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  • 1Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.


A new enantioselective rhodium-catalyzed domino reaction is described that gives access to fused heterocycles by desymmetrization of alkyne-tethered cyclohexadienones. Two new C-C bonds and two stereocenters are formed in one step with good enantioselectivity. In contrast to prior reports, it was found that a vinylidene is not involved in the product formation but that syn-addition of the rhodium-aryl species onto the alkyne takes place.

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