1085963-18-3Relevant academic research and scientific papers
Robust continuous-flow synthesis of deuterium-labeled ￠-nitroalcohols catalyzed by basic anion exchange resin
Cui, Sunliang,Ito, Naoya,Masuda, Hayato,Park, Kwihwan,Sajiki, Hironao,Teranishi, Wataru,Yamada, Tsuyoshi
, p. 1000 - 1006 (2020/09/22)
A practical and efficient continuous-flow system was developed for the synthesis of site-selectively deuterium-labeled ￠- nitroalcohols by using the tertiary amine-functionalized basic anion exchange resin, WA30, as a heterogeneous organocatalyst. For this system, WA30 was prepacked in a cartridge under metal-free conditions. The system was operated by pumping a solution of aldehydes or ketones, as electrophiles, and nitroalkanes in a solvent system of deuterium oxide and THF in the catalyst cartridge. Various deuterated ￠-nitroalcohols were obtained in moderate to excellent yields with high deuteration efficiencies. The continuous-flow system was applied in continuous synthesis for at least 72 h without degradation of the heterogeneous organocatalyst activity.
Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling
Yamada, Tsuyoshi,Kuwata, Marina,Takakura, Ryoya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
, p. 637 - 641 (2017/12/13)
A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).
Dual-reagent organocatalysis with a phosphine and electron-deficient alkene: application to the Henry reaction
Wang, Xiu,Fang, Fan,Zhao, Chen,Tian, Shi-Kai
scheme or table, p. 6442 - 6444 (2009/04/06)
Triphenylphosphine in combination with methyl acrylate was found to be able to catalyze the Henry (nitroaldol) reaction of various aldehydes and α-keto esters to give the corresponding β-nitroalkanols in good to excellent yields, and a catalytic cycle involving a zwitterionic phosphine-alkene adduct was proposed for this dual-reagent organocatalysis according to the deuterium-labeling experiments with CD3NO2.
