Catalytic Stereoselective [2,3]-Rearrangement Reactions

Thomas H. West, Stéphanie S.M. Spoehrle, Kevin Kasten, James E. Taylor, Andrew D. Smith

Research output: Contribution to journalReview article

59 Citations (Scopus)

Abstract

[2,3]-Sigmatropic rearrangement processes of allylic ylides or their equivalents can be applied to a variety of different substrates and generate products of wide interest/applicability to organic synthesis. This review describes the development and applications of stereoselective [2,3]-rearrangement reactions in which a substoichiometric amount of a catalyst is used in either the formation of the reactive intermediate or the [2,3]-rearrangement step itself.

Original languageEnglish
Pages (from-to)7446-7479
Number of pages34
JournalACS Catalysis
Volume5
Issue number12
DOIs
Publication statusPublished - 29 Oct 2015

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Keywords

  • allylic ammonium ylides
  • allylic N-oxides
  • allylic oxonium ylides
  • allylic sulfonium ylides
  • allylic sulfoxides
  • O-propargylic oximes
  • stereoselective catalysis
  • [2,3]-rearrangement

ASJC Scopus subject areas

  • Catalysis

Cite this

West, T. H., Spoehrle, S. S. M., Kasten, K., Taylor, J. E., & Smith, A. D. (2015). Catalytic Stereoselective [2,3]-Rearrangement Reactions. ACS Catalysis, 5(12), 7446-7479. https://doi.org/10.1021/acscatal.5b02070