Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives.
The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.
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
Manzano
Pilar
P
Montero
Carlos
C
Priego
Julián
J
Viso
Alma
A
Cano
Félix H
FH
Martínez-Alcázar
María Paz
MP