561319-66-2Relevant academic research and scientific papers
Nucleophilic epoxidation of γ-hydroxyvinyl sulfoxide derivatives
Fernandez de la Pradilla, Roberto,Buergo, Maria Victoria,Manzano, Pilar,Montero, Carlos,Priego, Julian,Viso, Alma,Cano, Felix H.,Martinez-Alcazar, Maria Paz
, p. 4797 - 4805 (2007/10/03)
The nucleophilic epoxidation of simple (γ-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the γ 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.
