Triflic acid catalyzed synthesis of spirocycles via acetylene cations

Tienan Jin, Masafumi Himuro, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)

Abstract

Rings of various shapes and sizes: Spirocyclic hydrocarbons 2 were obtained in good to excellent yield through the triflic acid (TfOH) catalyzed cyclization of alkynyl-substituted cyclic tertiary alcohols 1 under mild conditions with good control of ring size (see scheme). The method was extended to the synthesis of bridged bicyclic ketones with high stereoselectivity.

Original languageEnglish
Pages (from-to)5893-5896
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number32
DOIs
Publication statusPublished - 2009 Jul 27

Keywords

  • Alkynes
  • Cyclization
  • Spirocycles
  • Tertiary alcohols
  • Triflic acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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