Metal-catalyzed oxidation and epoxidation of alpha-hydroxy vinyl and dienyl sulfoxides.
Treatment of acyclic alpha-hydroxyalkyl alpha,beta-unsaturated sulfoxides with t-BuOOH/VO(acac)2 results in rapid oxidation to the unsaturated sulfones followed by an unusual regio- and stereoselective epoxidation at the unsaturated sulfones; this methodology has been applied to the preparation of carbohydrate-like fragments.
Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
Roberto
R
Fernández de la Pradilla
Alejandro
A
Castellanos
Jorge
J
Fernández
Milagros
M
Lorenzo
Pilar
P
Manzano
Paloma
P
Méndez
Julián
J
Priego
Alma
A
Viso