203207-92-5

Basic information

• Product Name: (2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine
• Synonyms: (2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine
• CAS NO: 203207-92-5
• Molecular Weight: 659.943
• Mol File: 203207-92-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine(203207-92-5)
• EPA Substance Registry System: (2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine(203207-92-5)

Safety Data

• Hazardous Substances Data: 203207-92-5(Hazardous Substances Data)

Upstream product

• 106-45-6 para-thiocresol 
• 120483-06-9 3-p-Tolylsulfanyl-propionaldehyde 
• 203207-84-5 N-[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-5,5-dimethoxy-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide 

Relevant articles and documents

1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis. Highly regio- and stereoselective SN1′ and alkylation reactions

Reaction of lithiated β-sulfonyl acetals with amino acid-derived N-tosylaziridines followed by acid-catalysed cyclisation gives enantiomerically pure 2-alkyl 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines 3 in good yields. These heterocyclic substrates react efficiently and highly stereoselectively with a range of carbon nucleophiles under Lewis acidic conditions to give the 1,2,5,6-tetrahydropyridine products of SN1′ reaction, and undergo lithiation followed by completely stereoselective reaction at the 4-position with haloalkanes.