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

Tomoya Miura, Masahiko Shimada, Paula De Mendoza, Carl Deutsch, Norbert Krause, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)

Abstract

(Chemical Equation Presented) A rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids affords syn-configured α-allenols with high diastereoselectivity. The reaction is initiated by addition of an arylrhodium(I) species onto the alkyne moiety of the alkynyl oxirane. The resulting alkenylrhodium(I) intermediate undergoes β-oxygen elimination to open the oxirane ring in a syn-selective fashion. Protonolysis of the rhodium(I) alkoxide with arylboronic acid releases the corresponding α-allenol along with the rhodium(I) boronate, which undergoes β-aryl elimination to regenerate the arylrhodium(I) species. The utility of this method is demonstrated by an application to a concise synthesis of (±)-Boivinianin B.

Original languageEnglish
Pages (from-to)6050-6054
Number of pages5
JournalJournal of Organic Chemistry
Volume74
Issue number16
DOIs
Publication statusPublished - 2009
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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