107624-49-7Relevant articles and documents
Relay iron/chiral bronsted acid catalysis: Enantioselective hydrogenation of benzoxazinones
Lu, Liang-Qiu,Li, Yuehui,Junge, Kathrin,Beller, Matthias
, p. 2763 - 2768 (2015)
An asymmetric hydrogenation reaction of benzoxazinones has been accomplished via a relay iron/chiral Bronsted acid catalysis. This approach provides a variety of chiral dihydrobenzoxazinones in good to high yields (75-96%) and enantioselectivities (up to
Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds
Chen, Fushan,Deng, Li,Dong, Wenjin,Tang, Jie,Xian, Mo
, p. 5564 - 5569 (2021/08/25)
A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.
Renewable Molecular Flasks with NADH Models: Combination of Light-Driven Proton Reduction and Biomimetic Hydrogenation of Benzoxazinones
Zhao, Liang,Wei, Jianwei,Lu, Junhua,He, Cheng,Duan, Chunying
supporting information, p. 8692 - 8696 (2017/07/17)
Using small molecules with defined pockets to catalyze chemical transformations resulted in attractive catalytic syntheses that echo the remarkable properties of enzymes. By modulating the active site of a nicotinamide adenine dinucleotide (NADH) model in a redox-active molecular flask, we combined biomimetic hydrogenation with in situ regeneration of the active site in a one-pot transformation using light as a clean energy source. This molecular flask facilitates the encapsulation of benzoxazinones for biomimetic hydrogenation of the substrates within the inner space of the flask using the active sites of the NADH models. The redox-active metal centers provide an active hydrogen source by light-driven proton reduction outside the pocket, allowing the in situ regeneration of the NADH models under irradiation. This new synthetic platform, which offers control over the location of the redox events, provides a regenerating system that exhibits high selectivity and efficiency and is extendable to benzoxazinone and quinoxalinone systems.