Sulfoxides in Julia-Lythgoe olefination: efficient and stereoselective preparation of di-, tri-, and tetrasubstituted olefins.
[reaction: see text] A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI2/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.
Pospísil
Jirí
J
Université Catholique de Louvain, Département de Chimie, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium.
Pospísil
Tomás
T
Markó
István E
IE