159425-79-3

Basic information

• Product Name: (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol
• Synonyms: (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol
• CAS NO: 159425-79-3
• Molecular Weight: 547.877
• Mol File: 159425-79-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol(159425-79-3)
• EPA Substance Registry System: (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol(159425-79-3)

Safety Data

• Hazardous Substances Data: 159425-79-3(Hazardous Substances Data)

Upstream product

• 159425-78-2 (1S,2R,S_S)-2-methyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 4381-25-3 (S)-S-methyl-S-phenylsulfoximine 
• 1728-46-7 2-tert-butylcyclohexanone 
• 140146-08-3 (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 

Downstream Products

• 98104-30-4 trans 2-tert-butylcyclohexanol 
• 13492-06-3 (S,S)-cis-2-tert-butylcyclohexanol 
• 159425-78-2 (1S,2R,S_S)-2-methyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 
• 14132-21-9 (-)-2-tert-butylcyclohexanone 
• 140146-08-3 (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 

Relevant articles and documents

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.