Stereospecific Synthesis of Cyclobutylboronates through Copper(I)-Catalyzed Reaction of Homoallylic Sulfonates and a Diboron Derivative
Stereospecific Synthesis of Cyclobutylboronates through Copper(I)-Catalyzed Reaction of Homoallylic Sulfonates and a Diboron Derivative
复制标题
DOI：
10.1021/ja101793a
复制
发表时间：
2010-05-05
影响因子：
15
通讯作者：
Sawamura, Masaya
中科院分区：
文献类型：
--
作者：
Ito, Hajime;Toyoda, Takashi;Sawamura, Masaya
报道了铜(I)催化的立体定向反应，用于制备顺式和反式-1-甲硅烷基-2-硼基环丁烷以及1-苯基-2-硼基环丁烷。在 CuCl/dppp 催化剂、双(频哪醇)二硼和 K(O-t-Bu)/THF 存在下，(Z)-和(E)-同烯丙基甲磺酸盐分别转化为相应的反式和顺式环丁烷衍生物。进行顺式和反式硼基环丁烷的立体定向衍生化以证明硼基环丁烷的实用性。
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.