Co-catalyzed autoxidation of alkene in the presence of silane. The effect of the structure of silanes on the efficiency of the reaction and on the product distribution

Jin Ming Wu, Shigeki Kunikawa, Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A systematic investigation of the structural effect of silanes on the Co-catalyzed reductive oxygenation of alkene in the presence of silane (Mukaiyama-Isayama reaction) showed that the efficiency of the reaction decreases with the increase of the steric bulk of the silanes. A similar trend was observed for the metal-exchange reaction between Co(III)-alkylperoxo complex and silane, too. The peroxidation of (S)-limonene, followed by deprotection of the derived silyl peroxides, provides a mixture of the corresponding monocyclic hydroperoxide 24 and the bicyclic one 25, the ratio being a marked function of the steric bulk of silanes.

Original languageEnglish
Pages (from-to)9961-9968
Number of pages8
JournalTetrahedron
Volume61
Issue number42
DOIs
Publication statusPublished - Oct 17 2005

Keywords

  • Antimalarial activity
  • Co-catalyzed autoxidation
  • Silyl peroxide
  • Yingzhaosu A analogue

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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