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

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

Organic letters (2013-02-21)
Juliane Keilitz, Stephen G Newman, Mark Lautens
RESUMO

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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Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis