Palladium-catalyzed stereospecific epoxide-opening reaction of gamma,delta-epoxy-alpha,beta-unsaturated esters with an alkylboronic acid leading to gamma,delta-vicinal diols with double inversion of the configuration.
A palladium-catalyzed stereospecific epoxide-opening reaction of gamma,delta-epoxy-alpha,beta-unsaturated esters with an alkylboronic acid leading to gamma,delta-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive S(N)2 processes, to afford the corresponding gamma,delta-cyclic boronates in high yields.
Division of Chemistry, Graduate School of Science, Hokkaido University, 060-0810 Sapporo, Japan.
Atsushi
A
Hirai
Xiao-Qiang
XQ
Yu
Terumichi
T
Tonooka
Masaaki
M
Miyashita