122833-94-7

Upstream product

• 4294-57-9 para-methylphenylmagnesium bromide 
• 257276-66-7 [R_S]-(-)-cholesteryl (E)-3,3-dimethyl-1-butenesulfinate 
• 630-19-3 pivalaldehyde 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 122920-83-6 1-((R)-(1R,2S)-2-tert-Butyl-4-methylene-cyclopentanesulfinyl)-4-methyl-benzene 
• 122833-97-0 1-((R)-(1S,2R)-2-tert-Butyl-4-methylene-cyclopentanesulfinyl)-4-methyl-benzene 
• 148005-10-1 (S)-(E)-2,2,6,6-tetramethyl-4-<(S)-p-tolylsulfinyl>hept-4-en-3-ol 
• 148005-09-8 (R)-(E)-2,2,6,6-tetramethyl-4-<(S)-p-tolylsulfinyl>hept-4-en-3-ol 

Relevant 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

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.

Stereoselective Reactions of Lithio-vinylsulfoxides with Aldehydes

A series of homochiral vinyl sulfoxides-synthesised by treating vinyl Grignard reagents with homochiral menthyl toluene-p-sulfinate or sulfinyl oxazolidinones 8a and 9a- were deprotonated with LDS and allowed to react with acetaldehyde, isobutyraldehyde, and trimethylacetaldehyde to give β-hydroxy sulfoxides with moderate diastereoselectivity.The sulfoxide 1 gave the best selectivity with the larger aldehydes.The same diastereoselectivity, within experimental error, is observed in the reactions with trimethylacetaldehyde of both E-1 and Z-1 giving 85:15 and 84:16 mixtures of 2c and 3c respectively; evidently, the geometry of the vinyl group does not affect the selectivity.

ASYMMETRIC INDUCTION IN THE PALLADIUM CATALYZED CYCLOADDITION REACTION OF TRIMETHYLENEMETHANE WITH HOMOCHIRAL VINYLSULFOXIDES

The palladium catalyzed cycloaddition of trimethylenemethane with a variety of vinylsulfoxides led to cycloadducts in good to excellent chemical yields and with a good level of asymmetric induction.