title: Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative.
abstract: A copper(I)-catalyzed stereospecific reaction for the preparation of cis- and trans-1-silyl-2-borylcyclobutanes as well as 1-phenyl-2-borylcyclobutanes is reported. (Z)- and (E)-Homoallylic methanesulfonates were converted to the corresponding trans- and cis-cyclobutane derivatives, respectively, in the presence of a CuCl/dppp catalyst, bis(pinacolato)diboron, and K(O-t-Bu)/THF. Stereospecific derivatizations of the cis- and trans-borylcyclobutanes were carried out to demonstrate the utility of the borylcyclobutanes.
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan. hajito@sci.hokudai.ac.jp
authors.forename: Hajime
authors.initials: H
authors.lastname: Ito
authors.forename: Takashi
authors.initials: T
authors.lastname: Toyoda
authors.forename: Masaya
authors.initials: M
authors.lastname: Sawamura
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003503:Cyclobutanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D003503:Cyclobutanes; D003300:Copper