title: Iridium-catalyzed enantioselective allylic vinylation.
abstract: The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.
authors.affiliation: Eidgenössische Technische Hochschule Zürich, HCI H335, 8093 Zürich, Switzerland.
authors.forename: James Y
authors.initials: JY
authors.lastname: Hamilton
authors.forename: David
authors.initials: D
authors.lastname: Sarlah
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001881:Borates; D009942:Organometallic Compounds; D020005:Propanols; C006463:allyl alcohol; D007495:Iridium