Efficient Synthesis of O - Tert -Propargylic Oximes via Nicholas Reaction

Itaru Nakamura, Keigo Shiga, Mao Suzuki, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

Abstract

A synthetic protocol to access O - tert -propargylic oximes derived from tertiary propargylic alcohols was established via Nicholas reaction. Thus, BF 3·OEt 2-mediated reaction between the dicobalt hexacarbonyl complex of tert -propargylic alcohols and p -nitrobenzaldoxime followed by decomplexation with cerium(IV) ammonium nitrate afforded the corresponding O - tert -propargylic oximes in good to high yields. The obtained O - tert -propargylic oximes were effectively converted into heterocycles, such as four-membered cyclic nitrones, oxazepines, and isoxazolines, by using π-Lewis acidic catalysts.

Original languageEnglish
Pages (from-to)3461-3465
Number of pages5
JournalSynthesis (Germany)
Volume52
Issue number22
DOIs
Publication statusPublished - 2020 Nov 17

Keywords

  • Nicholas reaction
  • alkynes
  • gold catalysts
  • heterocycles
  • spirocycles
  • tertiary alcohols

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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