Stereoselective synthesis of α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids

Tomoya Miura, Masahiko Shimada, Sung Yu Ku, Tomohiro Tamai, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

69 Citations (Scopus)

Abstract

(Chemical Equation Presented) Better than Cu, Pd, and Fe catalysts: The rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids provides synconfigured α-allenols with excellent diastereoselectivity. Precoordination of the oxygen atom of the oxirane ring to rhodium is assumed to contribute to the high stereoselectivity as well as high reactivity.

Original languageEnglish
Pages (from-to)7101-7103
Number of pages3
JournalAngewandte Chemie - International Edition
Volume46
Issue number37
DOIs
Publication statusPublished - 2007
Externally publishedYes

Keywords

  • β-oxygen elimination
  • Addition
  • Allenes
  • Boron
  • Rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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