Microwave-assisted palladium(0)-catalyzed alkylative cyclization of allenyl aldehydes leading to 3-substituted 3-cycloalken-1-ols

Hirokazu Tsukamoto, Tomotaka Matsumoto, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

We have developed an efficient synthetic method for 3-substituted 3-cyclohexenols and -cyclopentenol based on Pd0-catalyzed alkylative, arylative, alkenylative, alkynylative, and borative cyclization reaction of allene-carbonyl compounds. Microwave irradiation increases not only the reaction rate but also the product yield by suppressing formation of hydroarylation byproducts observed in the same catalytic system. Cyclization of optically active 1,3-disubstituted allene aldehyde reveals that the reaction proceeds not through carbopalladation but through "anti-Wacker"-type oxidative addition.

Original languageEnglish
Pages (from-to)388-389
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number2
DOIs
Publication statusPublished - 2008 Jan 16

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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