title: Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents.
abstract: 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.
authors: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
authors: Juliane
authors: J
authors: Keilitz
authors: Stephen G
authors: SG
authors: Newman
authors: Mark
authors: M
authors: Lautens
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003510:Cyclohexanes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001896:Boron Compounds; D003510:Cyclohexanes; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D012238:Rhodium