145841-95-8Relevant articles and documents
Homochiral 2,3-epoxy sulfides - powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-...
Westwell, Andrew D.,Thornton-Pett, Mark,Rayner, Christopher M.
, p. 847 - 860 (2007/10/02)
The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described.These intermediates undergo elimination under basic reaction conditions to give (E)-γ-hydroxy-α,β-unsaturated sulfoxides, and under Lewis acidic conditions form novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydroxy sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulfoxides can also be converted into (E)-γ-hydroxy-α,β-unsaturated sulfoxides by elimination via cyclic sulfide.The synthesis of (E)-γ-hydroxy-α,β-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.
Lewis Acid Induced Reaction of 2,3-Epoxy Phenylsulphoxides.
Rayner, Christopher M.,Westwell, Andrew D.
, p. 2409 - 2412 (2007/10/02)
The regio- and stereocontrolled hydrolysis of diastereomerically pure 2,3-epoxy phenylsulphoxides via novel sulphoxonium salts generated under Lewis acidic conditions is described.
