140146-08-3

Upstream product

• 4381-25-3 (S)-S-methyl-S-phenylsulfoximine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 159425-79-3 (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 
• 159425-78-2 (1S,2R,S_S)-2-methyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 

Downstream Products

• 131558-87-7 C₃₄H₄₂N₂OSSi 
• 131558-87-7 C₃₄H₄₂N₂OSSi 
• 131558-97-9 C₂₈H₃₇NO₂SSi 
• 131558-97-9 C₂₈H₃₇NO₂SSi 
• 159425-79-3 (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 
• 159425-78-2 (1S,2R,S_S)-2-methyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 

Relevant academic research and scientific papers

Chiral Sulfur Compounds. Part 25. Diastereoselective 1,2-Additions of Lithiated (+)-(S)-N-tert-Butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to Ketones

Lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 2f reacts with prochiral ketones to give a mixture of diastereomeric β-hydroxy sulfoximine adducts with a diastereoselection ranging from 79:21 to 98:2 depending upon the steric demand of the ketone.Racemic chiral cyclic ketones react with 2f to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts which could be separated by a combination of column chromatography and recrystallization.Thermolysis of the diastereoisomerically pure adducts gave 2-alkylcyclohexanones in high enantiomeric purity.The relative stereochemistries of four of the β-hydroxy sulfoximine adducts have been unequivocally determined from single-crystal X-ray structural analysis.The stereochemical outcome of these 1,2-additions can best be rationalized by invoking competing boat transition states.