203207-90-3

Upstream product

• 124575-31-1 (S)-2-isobutyl-1-tosyl-aziridine 
• 106-45-6 para-thiocresol 
• 120483-06-9 3-p-Tolylsulfanyl-propionaldehyde 
• 203207-82-3 N-[(S)-1-Isobutyl-5,5-dimethoxy-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide 

Downstream Products

• 277742-71-9 Acetic acid (2R,3S,4S,6S)-3-acetoxy-6-isobutyl-1,4-bis-(toluene-4-sulfonyl)-piperidin-2-yl ester 
• 277742-77-5 (2R,3S,4S,6S)-2-Allyl-6-isobutyl-1,4-bis-(toluene-4-sulfonyl)-piperidin-3-ol 
• 277742-67-3 (2R,3S,4S,6S)-6-Isobutyl-1,4-bis-(toluene-4-sulfonyl)-piperidine-2,3-diol 

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.