title: Synthesis of vicinal dimethyl chirons by asymmetric hydrogenation of trisubstituted alkenes.
abstract: Roche ester derivatives were converted to trisubstituted alkenes with allylic chiral centers. Hydrogenation of these substrates with chiral analogues of Crabtree's catalyst, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst controlled. However, the peripheral functionalities and protecting groups had significant effects and could be adjusted to give high stereoselectivities. The upshot of this work is that alpha,omega-functionalized chirons to introduce 1,2-dimethyl functionalities into acyclic chains have been developed.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, Texas 77840, USA.
authors.forename: Jian
authors.initials: J
authors.lastname: Zhao
authors.forename: Kevin
authors.initials: K
authors.lastname: Burgess
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D008697:Methane / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D010080:Oxazoles; D008697:Methane