1037238-05-3Relevant articles and documents
Enantioselective C-H Alkenylation of Ferrocenes with Alkynes by Half-Sandwich Scandium Catalyst
Lou, Shao-Jie,Zhuo, Qingde,Nishiura, Masayoshi,Luo, Gen,Hou, Zhaomin
, p. 2470 - 2476 (2021)
The enantioselective C-H alkenylation of ferrocenes with alkynes is, in principle, a straightforward and atom-efficient route for the construction of planar-chiral ferrocene scaffolds bearing alkene functionality but has remained scarcely explored to date. Here we report for the first time the highly enantioselective C-H alkenylation of quinoline- and pyridine-substituted ferrocenes with alkynes by a half-sandwich scandium catalyst. This protocol features broad substrate scope, high enantioselectivity, and 100% atom efficiency, selectively affording a new family of planar-chiral ferrocenes bearing N/alkene functionalities. The mechanistic details have been clarified by DFT analyses. The use of a quinoline/alkene-functionalized ferrocene product as a chiral ligand for asymmetric catalysis is also demonstrated.
Chiral dihydrobenzofuran-based diphosphine (BICMAP): Optical resolution and application to rhodium(I)-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to cyclic enones
Mino, Takashi,Hashimoto, Masatoshi,Uehara, Katsunori,Naruse, Yoshiaki,Kobayashi, Shohei,Sakamoto, Masami,Fujita, Tsutomu
, p. 4562 - 4564 (2012)
Chiral dihydrobenzofuran-based diphosphine ligand (BICMAP) 1 was used as a ligand for the rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to cyclic enones up to 99% ee. We also found that the BICMAP-rhodium system was an efficient catalyst for the 1,4-addition of alkenylboronic acids to 2-cyclohexenone in good enantioselectivities.
Enantio- and Diastereodivergent Synthesis of Spirocycles through Dual-Metal-Catalyzed [3+2] Annulation of 2-Vinyloxiranes with Nucleophilic Dipoles
Huo, Xiaohong,Luo, Yicong,Peng, Youbin,Wu, Liang,Zhang, Wanbin
supporting information, p. 24941 - 24949 (2021/10/25)
The development of efficient and straightforward methods for obtaining all optically active isomers of structurally rigid spirocycles from readily available starting materials is of great value in drug discovery and chiral ligand development. However, the
Polymer-incarcerated chiral Rh/Ag nanoparticles for asymmetric 1,4-addition reactions of arylboronic acids to enones: Remarkable effects of bimetallic structure on activity and metal leaching
Yasukawa, Tomohiro,Miyamura, Hiroyuki,Kobayashi, Shu
, p. 16963 - 16966 (2013/01/15)
Robust and highly active bimetallic Rh nanoparticle (NP) catalysts, PI/CB Rh/Ag, have been developed and applied to the asymmetric 1,4-addition of arylboronic acids to enones without leaching of the metals. We found that the structures of the bimetallic Rh/Ag catalysts and chiral ligands strongly affect their catalytic activity and the amount of metal leaching. PI/CB Rh/Ag could be recycled several times by simple operations while keeping high yields and excellent enantioselectivities. To show the versatility of the PI/CB Rh/Ag catalyst, a one-pot, oxidation-asymmetric 1,4-addition reaction of an allyl alcohol and an arylboronic acid was demonstrated by combining the PI/CB Rh/Ag catalyst with PI/CB Au as an aerobic oxidation catalyst.
Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: A simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions
Feng, Xiangqing,Wei, Beibei,Yang, Jing,Du, Haifeng
supporting information; experimental part, p. 5927 - 5929 (2011/10/08)
One novel type of chiral olefin/sulfinimide hybrid ligands has been developed through a simple one-step condensation of α,β-unsaturated ketones with tert-butanesulfinamide and utilized successfully for rhodium-catalyzed asymmetric conjugated additions to furnish the desired adducts in high yields with excellent ee's.