Eu(OTf)3-Catalyzed highly regioselective nucleophilic ring opening of 2,3-epoxy alcohols: An efficient entry to 3-substituted 1,2-diol derivatives

Shun Ichiro Uesugi, Tsubasa Watanabe, Takamichi Imaizumi, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4408-4411
Number of pages4
JournalOrganic letters
Volume16
Issue number17
DOIs
Publication statusPublished - 2014 Sep 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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