Sulfoxides in Julia-Lythgoe olefination: Efficient and stereoselective preparation of Di-, Tri-, and tetrasubstituted olefins

Pospisil, Jiri;Pospisil, Tomas;Marko, Istvan
(2005) Organic Letters — Vol. 7, n° 12, p. 2373-2376 (2005)

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Authors
  • Pospisil, JiriUCLouvain
    Author
  • Pospisil, TomasUCLouvain
    Author
  • Marko, IstvanUCLouvain
    Author
Abstract
A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SMl(2)/HMPA- or DMPU-mediated reductive elimination, 1,2-di-, tri-, and tetrasubstituted olefins in moderate to excellent yields and E/Z selectivity. The conditions are mild, and the procedure is broadly applicable.
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Pospisil, J., Pospisil, T., & Marko, I. (2005). Sulfoxides in Julia-Lythgoe olefination: Efficient and stereoselective preparation of Di-, Tri-, and tetrasubstituted olefins. Organic Letters, 7(12), 2373-2376. https://doi.org/10.1021/ol050649e (Original work published 2005)