Carbamate as an accelerating group in intermolecular Pauson-Khand reaction

Shota Asano, Kaori Itto-Nakama, Hirokazu Arimoto

Research output: Contribution to journalArticle

Abstract

The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).

Original languageEnglish
Article number151974
JournalTetrahedron Letters
Volume61
Issue number24
DOIs
Publication statusPublished - 2020 Jun 11

Keywords

  • Accelerating group
  • Carbamate
  • Cyclopentenone
  • Intermolecular
  • Pauson-Khand reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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