Asymmetric Sulfur-Ylide-Mediated Formal [4+1]-Annulation Reaction: Scope and Mechanism

Clergue, Sébastien;Rousseau, Olivier;Delaunay, Thierry;Dequirez, Geoffroy;Robiette, Raphaël;et.al.
(2018) Chemistry: A European Journal — Vol. 24, n° 44, p. 11417-11425 (2018)

Files

Robiette-Full_Paper_revised.pdf
  • Open Access
  • Adobe PDF
  • 4.03 MB
Download

Details

Authors
Show more
Abstract
A formal (4+1)‐annulation strategy between sulfur ylides and 1,3‐dienes was developed to afford functionalized cyclopentanoids. The process consists of a stereoselective cyclopropanation reaction followed, in situ, by a stereospecific MgI2‐catalyzed vinylcyclopropane–cyclopentene rearrangement. The use of chiral sulfur ylides provided cyclopentanoids with excellent enantiocontrol. A combined experimental and computational mechanistic study showed that the stereospecificity of the rearrangement could be accounted for by a double SN2 reaction mechanism involving iodide.
Affiliations

Citations

  • APA
  • Chicago
  • FWB

Clergue, S., Rousseau, O., Delaunay, T., Dequirez, G., Tran, T.-V., El Aakchioui, S., Barozzino Consiglio, G., & Robiette, R. (2018). Asymmetric Sulfur-Ylide-Mediated Formal [4+1]-Annulation Reaction: Scope and Mechanism. Chemistry: A European Journal, 24(44), 11417-11425. https://doi.org/10.1002/chem.201801874 (Original work published 2018)