1354648-84-2Relevant academic research and scientific papers
Dihydrophenanthridine: A new and easily regenerable NAD(P)H model for biomimetic asymmetric hydrogenation
Chen, Qing-An,Gao, Kai,Duan, Ying,Ye, Zhi-Shi,Shi, Lei,Yang, Yan,Zhou, Yong-Gui
, p. 2442 - 2448 (2012)
A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regenerat
Chiral and Regenerable NAD(P)H Models Enabled Biomimetic Asymmetric Reduction: Design, Synthesis, Scope, and Mechanistic Studies
Luo, Gen,Luo, Yi,Wang, Jie,Zhao, Yanan,Zhao, Zi-Biao,Zhou, Yong-Gui,Zhu, Zhou-Hao
, (2020/01/31)
The coenzyme NAD(P)H plays an important role in electron as well as proton transmission in the cell. Thus, a variety of NAD(P)H models have been involved in biomimetic reduction, such as stoichiometric Hantzsch esters and achiral regenerable dihydrophenantheridine. However, the development of a general and new-generation biomimetic asymmetric reduction is still a long-term challenge. Herein, a series of chiral and regenerable NAD(P)H models with central, axial, and planar chiralities have been designed and applied in biomimetic asymmetric reduction using hydrogen gas as a terminal reductant. Combining chiral NAD(P)H models with achiral transfer catalysts such as Br?nsted acids and Lewis acids, the substrate scope could be also expanded to imines, heteroaromatics, and electron-deficient tetrasubstituted alkenes with up to 99% yield and 99% enantiomeric excess (ee). The mechanism of chiral regenerable NAD(P)H models was investigated as well. Isotope-labeling reactions indicated that chiral NAD(P)H models were regenerated by the ruthenium complex under hydrogen gas first, and then the hydride of NAD(P)H models was transferred to unsaturated bonds in the presence of transfer catalysts. In addition, density functional theory calculations were also carried out to give further insight into the transition states for the corresponding transfer catalysts.
Catalytic Biomimetic Asymmetric Reduction of Alkenes and Imines Enabled by Chiral and Regenerable NAD(P)H Models
Wang, Jie,Zhu, Zhou-Hao,Chen, Mu-Wang,Chen, Qing-An,Zhou, Yong-Gui
supporting information, p. 1813 - 1817 (2019/01/22)
The development of biomimetic chemistry based on the NAD(P)H with hydrogen gas as terminal reductant is a long-standing challenge. Through rational design of the chiral and regenerable NAD(P)H analogues based on planar-chiral ferrocene, a biomimetic asymm
