34553-13-4Relevant academic research and scientific papers
Stereospecific Grignard reactions of cholesteryl 1-alkenesulfinate esters: Application of the Andersen protocol to the preparation of non-racemic α,β-unsaturated sulfoxides
Strickler, Rick R.,Motto, John M.,Humber, Craig C.,Schwan, Adrian L.
, p. 423 - 430 (2003)
Enantiomerically enriched α,β-unsaturated sulfinate esters of (-)-cholesterol undergo stereospecific substitutions at sulfur when treated in benzene at 6°C with Grignard reagents. Sulfoxides with ees of 85-99.5% are obtained when enantiopure sulfinates are used. The substitution reactions proceed with inversion of sulfur configuration. Enantiomerically pure cholesteryl (E)-2-carbomethoxyethenesulfinate is not a suitable reactant under the Grignard reaction conditions. It is suggested that the ester group induces unwanted reactions significantly lowering both the yield and sulfur stereogenicity.
