title: A highly enantioselective and diastereoselective synthesis of cyclobutanes via boronic esters.
abstract: [formula: see text] Deprotonation of enantiopure (R,R)-1,2-dicyclohexyl-1,2-ethanediol 1-chloro-4-cyanobutylboronates 5 with LDA followed by treatment with anhydrous magnesium bromide yields (R)-(trans-2-cyanocyclobutyl)boronic esters 7 in high diastereomeric and enantiomeric purity. No cyclobutane formation has been observed in the absence of at least a catalytic amount of magnesium halide.
authors.affiliation: Department of Chemistry, Washington State University, Pullman 99164-4630, USA.
authors.forename: H W
authors.initials: HW
authors.lastname: Man
authors.forename: W C
authors.initials: WC
authors.lastname: Hiscox
authors.forename: D S
authors.initials: DS
authors.lastname: Matteson
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002087:Butyrates / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis*; D004952:Esters; D008274:Magnesium / Q000737:chemistry; D013058:Mass Spectrometry; D009570:Nitriles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D002087:Butyrates; D003503:Cyclobutanes; D004952:Esters; D009570:Nitriles; D008274:Magnesium