145198-91-0Relevant 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
Bando,Harayama,Fukazawa,Shiro,Fugami,Tanaka,Tamaru
, p. 1465 - 1474 (1994)
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
Tamaru, Yoshinao,Bando, Takashi,Kawamura, Youichi,Okamura, Kazuto,Yoshida, Zen-ichi,Shiro, Motoo
, p. 1498 - 1500 (2007/10/02)
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.
