1402166-99-7Relevant academic research and scientific papers
Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water
Chen, Yang,Liu, Changmeng,Xu, Dong,Xu, Jiaxi,Yang, Zhanhui
supporting information, p. 6050 - 6058 (2021/08/23)
An iridium-catalyzed highly chemoselective and efficient transfer hydrogenation reduction of structurally diverse nitroalkenes was realized at very low catalyst loading (S/C = up to 10000 or 20?000), using formic acid or sodium formate as a traceless hydride donor in water. Excellent functionality tolerance is also observed. The turnover number and turnover frequency of the catalyst reach as high as 18?600 and 19?200 h-1, respectively. An inert atmosphere protection is not required. The reactivities of nitroalkenes are dependent on their substitution pattern, and the pH value is a key factor to accomplish the complete conversion and excellent chemoselectivity. Purification of products is achieved by simple extraction without column chromatography. The reduction procedure is facilely amplified to 10 g scale at 10?000 S/C ratio. The potential of this green reduction in enantioselective hydrogenation has been demonstrated.
Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer
Hostmann, Theresa,Molloy, John J.,Bussmann, Kathrin,Gilmour, Ryan
supporting information, p. 10164 - 10168 (2019/12/24)
Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.
Rh-catalyzed highly enantioselective hydrogenation of nitroalkenes under basic conditions
Li, Shengkun,Huang, Kexuan,Zhang, Jiwen,Wu, Wenjun,Zhang, Xumu
supporting information, p. 10840 - 10844 (2013/09/02)
Go catalytic! A highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes and isomeric mixtures of nitroalkenes by using a Rh/DuanPhos catalytic system under basic conditions has furnished a convenient approach to β-chiral nitroalkanes, whic
Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes
Li, Shengkun,Huang, Kexuan,Cao, Bonan,Zhang, Jiwen,Wu, Wenjun,Zhang, Xumu
, p. 8573 - 8576 (2012/09/10)
Building the building blocks: A highly enantioselective hydrogenation of ?-aryl-?-alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.
