958029-28-2Relevant academic research and scientific papers
Silver-Catalyzed Asymmetric Insertion into Phenolic O?H Bonds using Aryl Diazoacetates and Theoretical Mechanistic Studies
Harada, Shingo,Tanikawa, Koki,Homma, Haruka,Sakai, Chigaya,Ito, Tsubasa,Nemoto, Tetsuhiro
supporting information, p. 12058 - 12062 (2019/07/12)
An enantioselective insertion reaction of silver carbenes generated from donor–acceptor-substituted diazo compounds into the O?H bond of phenols was developed. A homobinuclear silver complex with a chiral phosphorous ligand was created in situ from AgNTf
Rhodium(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O–H Bond Insertion of α-Diazo Esters
Zhang, Yiliang,Yao, Yuan,He, Li,Liu, Yang,Shi, Lei
, p. 2754 - 2761 (2017/08/23)
A rhodium(II)/chiral phosphoric acid system has been developed for the asymmetric catalytic insertion of α-diazo esters into the O–H bond of carboxylic acids to generate an array of synthetically useful α-hydroxy ester derivatives in good ee (up to 95% ee). Furthermore, the substrate scope could be successfully extended to a range of phenols and alcohols with high yield (up to 92%) and excellent enantioselectivity (up to 97%) under mild reaction conditions. Additionally, a density functional theory (DFT) study was performed to elucidate the reaction mechanism. (Figure presented.).
Enantioselective palladium-catalyzed insertion of α-aryl-α- diazoacetates into the O-H bonds of phenols
Xie, Xiu-Lan,Zhu, Shou-Fei,Guo, Jun-Xia,Cai, Yan,Zhou, Qi-Lin
supporting information, p. 2978 - 2981 (2014/04/03)
A palladium-catalyzed asymmetric O-H insertion reaction was developed. Palladium complexes with chiral spiro bisoxazoline ligands promoted the insertion of α-aryl-α-diazoacetates into the O-H bond of phenols with high yield and excellent enantioselectivity under mild reaction conditions. This palladium-catalyzed asymmetric O-H insertion reaction provided an efficient and highly enantioselective method for the preparation of synthetically useful optically active α-aryl-α-aryloxyacetates.
Chiral induction by Cinchona alkaloids in the rhodium(II) catalyzed O-H insertion reaction
Saito, Hiroaki,Iwai, Ryo,Uchiyama, Taketo,Miyake, Muneharu,Miyairi, Shinichi
scheme or table, p. 872 - 874 (2010/09/04)
Cinchona alkaloids are effective additives for enantioselective O-H insertion of α-phenyldiazoacetate and water by rhodium(II) complexes. Addition of silica gel promotes O-H insertion in the reaction rate and the reaction proceeds smoothly at less than the freezing point of water, e.g., -10°C, and provided mandelate in up to 50% ee. The results reported here are the highest asymmetric inductions obtained to date for O-H insertions via a Rh-carbenoid.
