247078-58-6Relevant articles and documents
Stereocontrolled synthesis of novel enantiomerically pure sulfides and selenides from (+)-camphor and (+)-camphor-10-sulfonyl chloride
Procter, David J.,Archer, Nicolas J.,Needham, Robert A.,Bell, David,Marchington, Allan P.,Rayner, Christopher M.
, p. 9611 - 9622 (2007/10/03)
Synthetic approaches to novel enantiomerically pure sulfides and selenides derived from (+)-camphor and (+)-camphor-10-sulfonate esters are described. Lewis acid mediated hemiacetal formation between a camphor- derived ketone and a thiol or selenol, and subsequent in situ reduction using triethylsilane selectively gives the exo-sulfide or -selenide in moderate overall yields. The initial sulfonate ester products can be converted into the corresponding sulfones by subsequent treatment with Grignard or organolithium reagents.