Indium(III)-catalyzed hydrative cyclization of 1,7-diynyl ethers

Org Lett. 2011 Aug 19;13(16):4280-3. doi: 10.1021/ol201624b. Epub 2011 Jul 15.

Abstract

A new hydrative cyclization of 1,7- and 1,8-diynyl ethers is reported. Using catalytic InI(3) and p-TSA as a cocatalyst, several 2,2-disubstituted tetrahydrofurans with exocyclic enone appendages were prepared. Reaction optimization and scope, mechanistic insight, and further transformation to a C-nucleoside analog are presented.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Cyclization
  • Ethers / chemistry*
  • Indium / chemistry*
  • Molecular Structure
  • Water / chemistry*

Substances

  • Ethers
  • Indium
  • Water