145198-97-6

Upstream product

• 145198-81-8 5-Methyl-4-vinyl-[1,3]dioxan-2-one 
• 145198-93-2 trans-N-(p-Toluenesulfonyl)-4-methyl-5-vinyl-6-aza-2-oxacyclohexan-1-one 
• 145198-93-2 cis-N-(p-Toluenesulfonyl)-4-methyl-5-vinyl-6-aza-2-oxacyclohexan-1-one 
• 4083-64-1 Tosyl isocyanate 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of 1,3-hydroxyl amines via palladium-catalyzed carbonate-carbamate transformation with unique stereoselectivity: Synthesis of 3-amino-4-penten-1-ols

The transformation of cyclic carbonates 1 to cyclic carbamates 4 is achieved in the presence of aryl or sulfonyl isocyanate by the catalysis of Pd(0) in high yield and with high structural flexibility. The reaction shows unique stereoselectivity: 3,4-disubstituted carbonates 2, irrespective of the composition of their stereoisomers, provide trans-5 exclusively or predominantly over cis-5. Mixtures of cis- and trans-3,5-disubstituted carbonates 3 furnish either cis-6 or trans-6 in high selectivity depending on the reaction conditions (kinetic or thermodynamic control, respectively). 1H NMR and X-ray structure analyses of 5 and 6 indicate that the stereochemical outcome is governed by an A1,2-strain between N-sulfonyl and C5-vinyl substituents.

Palladium-catalysed Regio- and Stereo-selective Synthesis of Allylic Amines

3-Vinyl-2,6-dioxacyclohexan-1-ones 1, by treatment with N-tosyl or N-arylisocyanates and a catalytic amount of Pd0, are converted into N-tosyl- and N-aryl-3-vinyl-2-aza-6-oxacyclohexan-1-ones 2 in good yields and with unique stereoselectivity.