1402166-86-2Relevant academic research and scientific papers
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.
Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers
Sim, Jae Hun,Song, Choong Eui
supporting information, p. 1835 - 1839 (2017/02/05)
Water enables new catalytic reactions for otherwise unreactive substrate systems. Under the “on water” reaction conditions, extremely unreactive β,β-disubstituted nitroalkenes smoothly underwent enantioselective Michael addition reactions with dithiomalonates using a chiral squaramide catalyst, affording both enantiomers of highly enantioenriched Michael adducts with all-carbon-substituted quaternary centers. The developed “on water” protocol was successfully applied for the scalable one-pot syntheses of chiral GABA analogs with all-carbon quaternary stereogenic centers at the β-position, which might show highly interesting pharmaceutical properties.
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
supporting information; experimental part, 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.
