title: Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.
abstract: Glycidols prepared via Sharpless asymmetric epoxidation participate in asymmetric redox-neutral carbonyl allylation with good levels of catalyst-directed diastereoselectivity. Equally stereoselective allylations may be performed from the aldehyde oxidation level using 2-propanol as the terminal reductant. An epoxide ring-opening reaction using AlMe3-n-BuLi is used to prepare the propionate-based stereotetrad spanning C17-C23 of dictyostatin, illustrating how this method may be applied to polyketide construction.
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Seung Wook
authors.initials: SW
authors.lastname: Kim
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Wonchul
authors.initials: W
authors.lastname: Lee
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Michael J
authors.identifier: 0000-0001-8418-9709
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000085:Acetates; D000498:Allyl Compounds; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006859:Hydrogen; D006865:Hydrogenation; D007495:Iridium; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000498:Allyl Compounds; D004852:Epoxy Compounds; D020005:Propanols; D007495:Iridium; D006859:Hydrogen; C498551:allyl acetate; C004312:glycidol