479623-82-0Relevant academic research and scientific papers
Nucleophilic epoxidation of α′-hydroxy vinyl sulfoxides
Fernandez de la Pradilla, Roberto,Fernandez, Jorge,Manzano, Pilar,Mendez, Paloma,Priego, Julian,Tortosa, Mariola,Viso, Alma,Martinez-Ripoll, Martin,Rodriguez, Ana
, p. 8166 - 8177 (2002)
The nucleophilic epoxidation of a variety of α′-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.
