827007-19-2Relevant articles and documents
Palladium Catalyzed Enantioselective Hayashi-Miyaura Reaction for Pharmaceutically Important 4-Aryl-3,4-dihydrocoumarins
Csuk, René,Lai, Jixing,Li, Shengkun,Song, Baoan,Yang, Chen
supporting information, p. 1329 - 1334 (2022/02/23)
The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins was successfully established, providing a straightforward asymmetric approach to achieving pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology features easily accessible and bench-stable ligands, a wide substrate scope, mild conditions, and accommodation of electron-withdrawing arylboronic acids.
Asymmetric Hydroesterification of Diarylmethyl Carbinols
Tian, Duanshuai,Xu, Ronghua,Zhu, Jinbin,Huang, Jianxun,Dong, Wei,Claverie, Jerome,Tang, Wenjun
, p. 6305 - 6309 (2021/02/09)
An efficient asymmetric hydroesterfication of diarylmethyl carbinols is developed for the first time with a Pd-WingPhos catalyst, resulting in a series of chiral 4-aryl-3,4-dihydrocoumarins in excellent enantioselectivities and good yields. The method features mild reaction conditions, a broad substrate scope, use of easily accessible starting materials, and low palladium loadings. A plausible stereochemical model is also proposed with the Pd-WingPhos catalyst. This method has enabled a 4-step asymmetric synthesis of (R)-tolterodine from readily available starting materials.
Organic Solvent-free Asymmetric 1,4-Addition in Liquid- or Solid-State using Conventional Stirring Catalyzed by a Chiral Rhodium Complex Developed as a Homogeneous Catalyst
Korenaga, Toshinobu,Kori, Hiroto,Asai, Shota,Kowata, Ryo,Shirai, Masayuki
, p. 6059 - 6066 (2020/10/28)
Organic solvent-free asymmetric 1,4-addition of arylboronic acids to enone substrates was performed by using a chiral rhodium complex catalyst developed as a homogeneous catalyst. Reactions catalyzed by [RhOH(cod)]2 with chiral diphosphine ligands in liquid- or solid-state proceeded to give chiral 1,4-adducts in high yield with enantioselectivities up to ca. 100 % ee by conventional stirring without mechanochemistry such as ball milling. The solid-state reactions under a static condition also proceeded, but with a slight decrease in enantioselectivity of the 1,4-adduct. SEM observations of the solid-state reactions indicated that no nanoparticles catalyst was generated. The organic solvent-free reaction could be applied to gram-scale synthesis by performing a greener purification using a minimum necessary organic solvent.
