177859-75-5Relevant academic research and scientific papers
Sulfoxide-controlled SN2′ displacements between cuprates and vinyl and alkynyl epoxy sulfoxides
Fernández De La Pradilla, Roberto,Viso, Alma,Castro, Sonia,Fernández, Jorge,Manzano, Pilar,Tortosa, Mariola
, p. 8171 - 8180 (2007/10/03)
The SN2′ displacement of readily available vinyl epoxy sulfoxides with organocopper reagents takes place in good yields with high anti selectivity and a good degree of E/Z stereocontrol to produce enantiopure α-hydroxy vinyl sulfoxides. A secon
Highly Stereoselective Nucleophilic Epoxidation of Simple Vinyl Sulfoxides
Fernández De La Pradilla, Roberto,Castro, Sonia,Manzano, Pilar,Martín-Ortega, María,Priego, Julián,Viso, Alma,Rodríguez, Ana,Fonseca, Isabel
, p. 4954 - 4966 (2007/10/03)
The nucleophilic epoxidation of readily available vinyl and dienyl sulfoxides with MOO-t-Bu (M = Li, Na, K) takes place in good yields, with complete preservation of double bond geometry in most cases and with moderate to excellent diastereofacial selectivity to produce enantio- and diastereomerically pure α,β-epoxy sulfoxides, valuable synthetic intermediates. Subsequent straightforward oxidation at sulfur affords the corresponding enantiopure sulfonyl oxiranes. For (1E)-2-sulfinyl dienes, the facial selectivity of this novel process may be controlled by the choice of metal (Li vs Na).
