Sulfur-directed synthesis of enantiopure hydroxy 2-sulfinyl butadienes.
The treatment of sulfinyl chlorohydrins with KO-t-Bu in THF generates epoxy vinyl sulfoxides that undergo an efficient base-induced rearrangement to generate enantiopure hydroxy 2-sulfinyl dienes. This novel process takes place with high chemo- and stereoselectivity. The chirality at sulfur effectively controls the geometry of the trisubstituted alkene.
Fernández de la Pradilla
Roberto
R
Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
Buergo
María Victoria
MV
Martínez
María Victoria
MV
Montero
Carlos
C
Tortosa
Mariola
M
Viso
Alma
A