Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative.
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.
Ito
Hajime
H
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan. hajito@sci.hokudai.ac.jp
Toyoda
Takashi
T
Sawamura
Masaya
M
D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003503:Cyclobutanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001688:Biological Products; D003503:Cyclobutanes; D003300:Copper