title: Inversion of the direction of stereoinduction in the coupling of chiral gamma,delta-unsaturated Fischer carbene complexes with o-ethynylbenzaldehyde.
abstract: [reaction: see text] A variety of gamma,delta-unsaturated carbene complexes that feature a stereogenic center at the beta-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is acyclic vs examples where it is within a ring.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
authors.forename: Binay K
authors.initials: BK
authors.lastname: Ghorai
authors.forename: Suneetha
authors.initials: S
authors.lastname: Menon
authors.forename: Dennis Lee
authors.initials: DL
authors.lastname: Johnson
authors.forename: James W
authors.initials: JW
authors.lastname: Herndon
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry*; D006838:Hydrocarbons; D007700:Kinetics; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D000480:Alkynes; D001547:Benzaldehydes; D006838:Hydrocarbons; D013256:Steroids; C413250:ethynylbenzaldehyde; C030011:carbene; D008697:Methane