title: Eu(OTf)3-catalyzed highly regioselective nucleophilic ring opening of 2,3-epoxy alcohols: an efficient entry to 3-substituted 1,2-diol derivatives.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University , Aobayama, Sendai 980-8578, Japan.
authors.forename: Shun-Ichiro
authors.initials: S
authors.lastname: Uesugi
authors.forename: Tsubasa
authors.initials: T
authors.lastname: Watanabe
authors.forename: Takamichi
authors.initials: T
authors.lastname: Imaizumi
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Shibuya
authors.forename: Naoki
authors.initials: N
authors.lastname: Kanoh
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D005063:Europium / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D003374:Coumarins; D008698:Mesylates; C498383:psymberin; D005063:Europium; C012077:trifluoromethanesulfonic acid