4.8 Review

Catalytic Stereoselective [2,3]-Rearrangement Reactions

Journal

ACS CATALYSIS
Volume 5, Issue 12, Pages 7446-7479

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02070

Keywords

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

Funding

  1. Royal Society
  2. European Research Council under the European Union [279850]
  3. European Union [PITH-GA-2013-607044]

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[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.

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