Copper Hydride Catalyzed Reductive Claisen Rearrangements

Kong Ching Wong, Elvis Ng, Wing Tak Wong, Pauline Chiu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

11 Citations (Scopus)

Abstract

KGaA, Weinheim. An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.
Original languageEnglish
Pages (from-to)3709-3712
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number11
DOIs
Publication statusPublished - 7 Mar 2016

Keywords

  • Claisen rearrangements
  • copper
  • hydride
  • reduction
  • silanes

ASJC Scopus subject areas

  • Chemistry(all)

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