2. Sulfur Ylide Epoxidations

An alternative route to epoxides is the reaction of sulfur ylides with carbonyl groups. Sulfur ylide epoxidation is a C-C bond forming process in addition to being a C-O bond forming process.


The use of chiral sulfides.

To date the highest enantioselectivites have been obtained by Durst3 and Solladie-Cavallo4

The results shown are for the preparation of trans-stilbene oxide using phase transfer conditons in which the ylide is generated in situ from the corresponding sulfonium salts in the presence of a base.

  1. Durst, T.; et al. Tetrahedron Asymm. , 1991, 2, 267. Durst, T.; et al. Tetrahedron Lett. , 1990, 31, 35.
  1. Solladie-Cavallo, A.; et al. Tetrahedron Asymm. , 1996, 7, 1783.


© 1997 Varinder Aggarwal