Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts

Ken S. Feldman, Michelle M. Bruendl

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Abstract

Several hydroxyalkynyliodonium triflates can be bicyclized with KNTMS2 to provide cyclopentannelated tetrahydrofuran derivatives in modest to good yields. The diastereoselectivity of C-H insertion by the intermediate carbene is better than that observed with the corresponding NTs analogs. Product lability and an electronic mismatch between hydroxide nucleophile and iodonium electrophile likely contribute to the modest yields.

Original languageEnglish (US)
Pages (from-to)2911-2914
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number19
DOIs
StatePublished - May 7 1998

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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