Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(iii) electrophile

Wei Ding, Jinkui Chai, Chen Wang, Junliang Wu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.

Original languageEnglish
Pages (from-to)8619-8624
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number19
DOIs
Publication statusPublished - 2020 May 13
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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