title: Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives.
abstract: A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK) http://www-gaunt.ch.cam.ac.uk.
authors.forename: Dean
authors.initials: D
authors.lastname: Holt
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK) http://www-gaunt.ch.cam.ac.uk. mjg32@cam.ac.uk.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Gaunt
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D009861:Onium Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002254:Carbonates; D009861:Onium Compounds; D020005:Propanols; C006463:allyl alcohol; D003300:Copper; D010100:Oxygen
keywords: copper; diols; homogeneous catalysis; hypervalent compounds; synthetic methods