1362858-72-7Relevant academic research and scientific papers
Method for preparing 3-substituted chromanone through nonmetal catalytic hydrogenation
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Paragraph 0139-0144, (2021/06/06)
The invention discloses a method for preparing 3-substituted chromanone through nonmetal catalytic hydrogenation. The method comprises the following step: in a catalytic system of oxazoline as shown in a formula I and borane as shown in a formula II, reacting a compound as shown in a formula VI with hydrogen to obtain the compound. According to the invention, the 3-substituted chromanone compound (formula V) is synthesized with high efficiency and high enantioselectivity by taking multiple substitution types of chromanone compounds (formula VI) as raw materials and hydrogen as a hydrogen source under the catalysis of oxazoline as shown in the formula I and borane as shown in the formula II; and the method has the advantages that the catalyst is easy to synthesize, the reaction condition is mild, the operation is simple and convenient, the stereoselectivity is high, the ee value of the product is as high as 95%, and the yield is as high as 98%.
Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System
Escudero-Casao, Margarita,Licini, Giulia,Orlandi, Manuel
supporting information, p. 3289 - 3294 (2021/04/07)
A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.
Asymmetric Hydrogenation of Ketones and Enones with Chiral Lewis Base Derived Frustrated Lewis Pairs
Du, Haifeng,Feng, Xiangqing,Gao, Bochao,Meng, Wei
supporting information, p. 4498 - 4504 (2020/02/05)
The concept of frustrated Lewis pairs (FLPs) has been widely applied in various research areas, and metal-free hydrogenation undoubtedly belongs to the most significant and successful ones. In the past decade, great efforts have been devoted to the synthesis of chiral boron Lewis acids. In a sharp contrast, chiral Lewis base derived FLPs have rarely been disclosed for the asymmetric hydrogenation. In this work, a novel type of chiral FLP was developed by simple combination of chiral oxazoline Lewis bases with achiral boron Lewis acids, thus providing a promising new direction for the development of chiral FLPs in the future. These chiral FLPs proved to be highly effective for the asymmetric hydrogenation of ketones, enones, and chromones, giving the corresponding products in high yields with up to 95 % ee. Mechanistic studies suggest that the hydrogen transfer to simple ketones likely proceeds in a concerted manner.
Enantioselective Synthesis of Isoflavanones by Catalytic Dynamic Kinetic Resolution
Qin, Tao,Metz, Peter
, p. 2981 - 2984 (2017/06/07)
A ruthenium-catalyzed asymmetric transfer hydrogenation of racemic isoflavanones with dynamic kinetic resolution yields virtually enantiopure isoflavanols as single diastereomers. Subsequent oxidation gives rise to isoflavanones in high enantiomeric purit
Arene CH-O hydrogen bonding: A stereocontrolling tool in palladium-catalyzed arylation and vinylation of ketones
Huang, Zhiyan,Lim, Li Hui,Chen, Zuliang,Li, Yongxin,Zhou, Feng,Su, Haibin,Zhou, Jianrong
, p. 4906 - 4911 (2013/06/05)
Weak is powerful: For the arylation of tin enolates, the palladium catalyst engages in weak CH-O hydrogen bonds to control stereoselectivity (see scheme). Similar catalysts capable of NH-O hydrogen bonding also works well. Copyright
