460357-62-4Relevant articles and documents
Eu(OTf)3-Catalyzed highly regioselective nucleophilic ring opening of 2,3-epoxy alcohols: An efficient entry to 3-substituted 1,2-diol derivatives
Uesugi, Shun-Ichiro,Watanabe, Tsubasa,Imaizumi, Takamichi,Shibuya, Masatoshi,Kanoh, Naoki,Iwabuchi, Yoshiharu
supporting information, p. 4408 - 4411 (2015/01/16)
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 protocol that effects a highly regioselective nucleophilic ring opening of 2,3- and 3,4-epoxy alcohols using various nucleophiles including alcohols, thiols, and unprotected amines are described.