97478-49-4

Upstream product

• 4192-77-2 ethyl cinnamate 
• 124994-14-5 cis-N-(p-tolylsulfonyl)-2-carbomethoxy-3-phenylaziridine 
• 103-26-4 Methyl cinnamate 
• 127-65-1 chloroamine-T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 104-55-2 3-phenyl-propenal 
• 70-55-3 toluene-4-sulfonamide 
• 97478-47-2 (2R,3S)-2-Hydroxy-3-phenyl-3-(toluene-4-sulfonylamino)-propionic acid ethyl ester 
• 50468-24-1 ethyl 3-phenyl-1-tosylaziridine-2-carboxylate 

Downstream Products

• 97478-38-1 5-ethenyl-2-phenyl-1-tosyl-3-pyrroline 
• 124994-24-7 5-isopropenyl-2-phenyl-1-tosyl-3-pyrroline 
• 124994-16-7 cis-3-(3-methyl-1,3-butadienyl)-2-phenyl-1-tosylaziridine 
• 97478-23-4 2-((E)-Buta-1,3-dienyl)-3-phenyl-1-(toluene-4-sulfonyl)-aziridine 
• 97478-23-4 cis-3-(1,3-butadienyl)-2-phenyl-1-tosylaziridine 

Relevant academic research and scientific papers

Copper-Catalyzed Aziridination with Redox-Active Ligands: Molecular Spin Catalysis

Small-molecule catalysts as mimics of biological systems illustrate the chemists’ attempts at emulating the tantalizing abilities displayed by nature's metalloenzymes. Among these innate behaviors, spin multistate reactivity is used by biological systems as it offers thermodynamic leverage towards challenging chemical reactivity but this concept is difficult to translate into the realm of synthetic organometallic catalysis. Here, we report a rare example of molecular spin catalysis involving multistate reactivity in a small-molecule biomimetic copper catalyst applied to aziridination. This behavior is supported by spin state flexibility enabled by the redox-active ligand.

TRANSFORMATION OF N-TOSYL-2-(1,3-BUTADIENYL)AZIRIDINE INTO N-TOSYL-2-ETHENYL-3-PYRROLINE.

1,3-Butadienylaziridines or 1,3-butadienylazetidines activated by N-tosyl group smoothly rearrange to vinylpyrroline derivatives or vinylpiperidines in the presence of a catalytic amount of Pd(PPh3)4.Triphenyltin radical induced rearrangement of title compounds is also described.

Pd(0) PROMOTED TRANSFORMATION OF N-TOSYL-2-(1,3-BUTADIENYL)-AZIRIDINE INTO N-TOSYL-2-VINYL-3-PYRROLINE

1,3-Butadienylaziridines activated by N-tosyl group smoothly rearrange to vinylpyrrolidine derivates in the presence of a catalytic amount of Pd(PPh3)4.Transformation of dienylazetidines into vinylpiperidine derivatives is also described.