Eu(OTf)<sub>3</sub>-Catalyzed Highly Regioselective Nucleophilic Ring Opening of 2,3-Epoxy Alcohols: An Efficient Entry to 3-Substituted 1,2-Diol Derivatives
作者:Shun-ichiro Uesugi、Tsubasa Watanabe、Takamichi Imaizumi、Masatoshi Shibuya、Naoki Kanoh、Yoshiharu Iwabuchi
DOI:10.1021/ol502264y
日期:2014.9.5
In our study of the total synthesis of (+)-irciniastatin A, we found a need to develop a method that enables a C3-selective nucleophilic ring opening of 2,3-epoxy alcohol by MeOH, by which we found that the use of combined catalytic amounts of Eu(OTf)3 and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) enables the intended transformation to obtain 3-methoxy-1,2-diol efficiently. Promising features of a
在我们对(+)-irciniastatin A的总合成的研究中,我们发现有必要开发一种方法,该方法能够使MeOH对2,3-环氧醇进行C3选择性亲核开环,从而发现使用Eu(OTf)3和2,6-二叔丁基-4-甲基吡啶(DTBMP)的组合催化量能够实现预期的转化,从而有效地获得3-甲氧基-1,2-二醇。描述了使用包括醇,硫醇和未保护的胺在内的各种亲核试剂实现2,3-和3,4-环氧醇的高度区域选择性亲核开环的方案的有前景的特征。