203207-88-9

Upstream product

• 203207-80-1 N-[(R)-1-Isopropyl-5,5-dimethoxy-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide 
• 106-45-6 para-thiocresol 
• 120483-06-9 3-p-Tolylsulfanyl-propionaldehyde 
• 62596-65-0 (2S)-2-isopropyl-1-[(4-methylphenyl)sulfonyl]aziridine 

Downstream Products

• 277742-66-2 (2R,3S,4S,6R)-6-Isopropyl-1,4-bis-(toluene-4-sulfonyl)-piperidine-2,3-diol 
• 404898-54-0 2-[(2R,4S)-2-Isopropyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridin-4-yl]-malonic acid dimethyl ester 
• 404898-65-3 2-[(2R,3R,4R,6R)-2,3-Diacetoxy-6-isopropyl-1-(toluene-4-sulfonyl)-piperidin-4-yl]-malonic acid dimethyl ester 
• 277742-70-8 Acetic acid (2R,3S,4S,6R)-3-acetoxy-6-isopropyl-1,4-bis-(toluene-4-sulfonyl)-piperidin-2-yl ester 
• 871511-09-0 (2R,4S)-2-Isopropyl-5-((E)-styryl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine 
• 871511-07-8 (2R,4S)-5-Isopropenyl-2-isopropyl-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine 
• 871511-05-6 (2R,4S)-2-(1-methylethyl)-1,4-bis(4-tolylsulfonyl)-5-vinyl-1,2,3,4-tetrahydropyridine 

Relevant academic research and scientific papers

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.