678196-17-3

Upstream product

• 51985-30-9 4-Methyl-N-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-benzenesulfonamide 
• 678196-13-9 Trifluoro-acetic acid (2R,4R)-4-acetoxy-2-[but-3-enyl-(toluene-4-sulfonyl)-amino]-4-phenyl-1-p-tolylsulfanyl-butyl ester 
• 678196-12-8 3-[N-(3-butenyl)-(4-methylphenyl)sulfonamido]-4-(S_S)(4-methylphenylsulfinyl)-1-phenyl-(1R,3R)-butyl acetate 
• 678196-15-1 ethyl 4-[N-(3-butenyl)-(4-methylphenyl)sulfonamido]-6-acetoxy-6-phenyl-(E,4R,6R)-2-hexenoate 
• 678196-11-7 4-(S_S)(4-methylphenylsulfinyl)-3-(4-methylphenylsulfonamido)-1-phenyl-(1R,3R)-butyl acetate 
• 678196-03-7 N-[2-bromo-3-hydroxy-1-(S_S)(4-methylphenylsulfinylmethyl)-3-phenyl-(1S,2R,3S)-propyl]-4-methyl-1-benzenesulfonamide 
• 678196-04-8 N-[3-hydroxy-1-(S_S)(4-methylphenylsulfinylmethyl)-3-phenyl-(1R,3R)-propyl]-4-methyl-1-benzenesulfonamide 
• 678196-02-6 4-methyl-1-[2-(S_R)(4-methylphenylsulfonamido)-4-phenyl-(2R,3E)-3-butenylsulfinyl]benzene 
• 678196-14-0 Acetic acid (1R,3R)-3-[but-3-enyl-(toluene-4-sulfonyl)-amino]-4-oxo-1-phenyl-butyl ester 
• 104-55-2 3-phenyl-propenal 
• 678196-16-2 2-[1-(4-methylphenylsulfonyl)-(2R)-1,2,5,6-tetrahydropyridin-2-yl]-1-phenyl-(1R)-ethyl acetate 

Downstream Products

• 497-89-2 2-[1-methyl-(2S)-piperidin-2-yl]-1-phenyl-(1R)-ethan-1-ol 
• 495-47-6 1-phenyl-2-[(2S)-piperidin-2-yl]-(1R)-ethan-1-ol 

Relevant academic research and scientific papers

Stereoselective synthesis of (-)-allosedamine and (1R,3R)-HPA-12 from β-p-toluenesulfonamido-γ,δ-unsaturated sulfoxide

A stereoselective synthesis of (-)-allosedamine and HPA-12 is disclosed. The key steps of the synthesis include the diastereoselective synthesis of a β-sulfonamido unsaturated sulfoxide, elaboration of a bromohydrin via intramolecular sulfinyl group participation and a ring-closing metathesis reaction for the construction of the piperidine ring of allosedamine.

Stereoselective synthesis of (-)-allosedamine

A stereoselective synthesis of (-)-allosedamine is disclosed. β-Aminosulfoxide 4 was generated stereoselectively by condensation of the sulfinyl anion 2 with N-Ts imine 3. The bromohydrin 5 was obtained by intramolecular sulfinyl group participation and the piperidine ring of allosedamine was elaborated using the ring-closing metathesis (RCM) reaction.