Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides

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16 Scopus citations

Abstract

The first highly enantioselective, diastereoselective, and regioselective [2,3]-rearrangement of iodonium ylides has been developed as a general solution to catalytic onium ylide rearrangements. In the presence of a chiral copper catalyst, substituted allylic iodides couple with α-diazoesters to generate metal-coordinated iodonium ylides, which undergo [2,3]-rearrangements with high selectivities (up to >95:5 r.r., up to >95:5 d.r., and up to 97 % ee). The enantioenriched iodoester products can be converted stereospecifically into a variety of onium ylide rearrangement products, as well as compounds that are not accessible by classical onium ylide rearrangements.

Original languageEnglish (US)
Pages (from-to)9868-9871
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number33
DOIs
StatePublished - 2017

Keywords

  • allylic compounds
  • copper
  • diazo compounds
  • rearrangements
  • ylides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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