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Keywords:

  • allylation;
  • ene reaction;
  • palladium;
  • sulfonyl chlorides;
  • umpolung
Thumbnail image of graphical abstract

Coupling up with sulfonyl chlorides: An ene reaction of alkenes with SO2⋅BCl3 permits the one-pot conversion of simple alkenes into β,γ-unsaturated sulfonyl chlorides or sulfinic silyl esters. These compounds can then be used as nucleophilic allylating agents with aldehydes and ketones to generate the corresponding homoallylic alcohols (see scheme) with good chemo- and diastereoselectivity in the presence of a suitable catalyst and reducing agent.