1143571-00-9Relevant academic research and scientific papers
Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
, p. 3294 - 3299 (2020/01/21)
A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
Chiral Phosphoric Acid Catalyzed Kinetic Resolution of Indolines Based on a Self-Redox Reaction
Saito, Kodai,Akiyama, Takahiko
, p. 3148 - 3152 (2016/03/12)
A strategy for oxidative kinetic resolution of racemic indolines was developed, employing salicylaldehyde derivative as the pre-resolving reagent and chiral phosphoric acid as the catalyst. The iminium intermediate, formed by the condensation reaction of an enantiomer of indoline with salicylaldehyde derivative, was hydrogenated by the same enantiomer of indoline to afford another enantiomer of indoline by a self-redox mechanism. The oxidative kinetic resolution of 2-aryl-substituted indolines proceeded to give enantiomers in good yields with excellent enantioselectivities.
Chiral phosphoric acid-catalyzed oxidative kinetic resolution of indolines based on transfer hydrogenation to imines
Saito, Kodai,Shibata, Yukihiro,Yamanaka, Masahiro,Akiyama, Takahiko
supporting information, p. 11740 - 11743 (2013/09/02)
The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities.
Kinetic resolution of indolines by Pd-catalyzed asymmetric ally Lie amination
Hou, Xue Long,Zheng, Bao Hui
supporting information; experimental part, p. 1789 - 1791 (2009/08/15)
The kinetic resolution of indolines was realized via a Pd-catalyzed allylic substitution reaction by using Trost's chiral ligand L10, affording optically active indolines and N-allylated indolines in high yields and high enantioselectivities with an 5 factor up to 59, which provided the first example for the kinetic resolution of nucleophiles via a transition-metal-catalyzed allylic substitution reaction. 2009 American Chemical Society.
