title: Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: application to the synthesis of the Californian red scale beetle pheromone.
abstract: E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF⋅3 H(2)O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF(2)/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Hesse
authors.forename: Craig P
authors.initials: CP
authors.lastname: Butts
authors.forename: Christine L
authors.initials: CL
authors.lastname: Willis
authors.forename: Varinder K
authors.initials: VK
authors.lastname: Aggarwal
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D001557:Benzenesulfonates / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism; D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D001517:Coleoptera / Q000378:metabolism; D003300:Copper / Q000737:chemistry; D004952:Esters; D006858:Hydrofluoric Acid / Q000737:chemistry; D008027:Light; D017680:Potassium Compounds / Q000737:chemistry; D012724:Sex Attractants / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: C573194:4-methylbenzenesulfonic acid; D000475:Alkenes; D001557:Benzenesulfonates; D001688:Biological Products; D004952:Esters; D017680:Potassium Compounds; D012724:Sex Attractants; C077003:potassium hydrogen fluoride; D003300:Copper; D001895:Boron; D006858:Hydrofluoric Acid