Organic Chemistry Portal



Stereospecific Synthesis of Cyclobutylboronates through Copper(I)-Catalyzed Reaction of Homoallylic Sulfonates and a Diboron Derivative

Hajime Ito*, Takashi Toyoda and Masaya Sawamura

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Email:

H. Ito, T. Toyoda, M. Sawamura, J. Am. Chem. Soc., 2010, 132, 5990-5992.

DOI: 10.1021/ja101793a

see article for more reactions


(E)- and (Z)-silyl and aryl-subsituted homoallylic methanesulfonates were converted to the corresponding cis- and trans-1-silyl-2-borylcyclobutanes as well as 1-phenyl-2-borylcyclobutanes in the presence of a CuCl/dppp catalyst, bis(pinacolato)diboron, and K(O-t-Bu)in THF. Stereospecific derivatizations of the cis- and trans-borylcyclobutanes were carried out to demonstrate the utility of the borylcyclobutanes.

see article for more examples

Key Words

cyclobutanes, alkylboronates

ID: J48-Y2010-1290