title: Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols.
abstract: In this report, zirconium(IV)- and hafnium(IV)-bishydroxamic acid complexes were utilized in the highly enantioselective epoxidation of homoallylic alcohols and bishomoallylic alcohols, which used to be quite difficult substrates for other types of asymmetric epoxidation reactions. The performance of the catalyst was improved by adding polar additive and molecular sieves. For homoallylic alcohols, the reaction could provide epoxy alcohols in up to 83% yield and up to 98% ee, while, for bishomoallylic alcohols, up to 79% yield and 99% ee of epoxy alcohols rather than cyclized tetrahydrofuran compounds could be obtained in most cases.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Li
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006195:Hafnium / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D015040:Zirconium / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D020005:Propanols; C006463:allyl alcohol; D015040:Zirconium; D006195:Hafnium