1197907-44-0Relevant academic research and scientific papers
Atroposelective Synthesis of Axially Chiral 4-Aryl α-Carbolines via N-Heterocyclic Carbene Catalysis
Ma, Rui,Wang, Xiaoxue,Zhang, Qiaoyu,Chen, Lei,Gao, Jian,Feng, Jie,Wei, Donghui,Du, Ding
, p. 4267 - 4272 (2021)
The first catalytic asymmetric construction of axially chiral 4-aryl α-carboline skeletons has been accomplished through an N-heterocyclic carbene (NHC)-catalyzed atroposelective formal [3 + 3] annulation of 4-nitrophenyl 3-arylpropiolates with 2-sulfonamidoindolines. The synthetic utility of the title compounds has been demonstrated by the diverse late-stage structural modifications. Density functional theory calculations were also conducted to illuminate the key factors for controlling the origin of the enantioselectivity. This strategy not only provides an efficient pathway to access axially chiral α-carboline atropisomers but also offers a novel catalytic enantioselective mode for the construction of axially chiral heterobiaryls by using NHC-bound alkynyl acylazoliums.
Enantioselective synthesis of Axially chiral hydroxy carboxylic acid derivatives by rhodium-catalyzed [2 〈 2 〈 2] cycloaddition
Ogaki, Shuichiro,Shibata, Yu,Noguchi, Keiichi,Tanaka, Ken
supporting information; experimental part, p. 1926 - 1929 (2011/06/24)
Axially chiral hydroxy carboxylic acid derivatives were successfully synthesized with high yields and ee values by the cationic rhodium(I)/axially chiral biaryl bisphosphine complex-catalyzed enantioselective [2 〈 2 〈 2] cycloaddition. Axially chiral hydroxy and dihydroxy carboxylic acid derivatives, bearing the aryl group at the ortho-position of the alkoxycarbonyl group, were also synthesized with high regio- and enantioselectivity.
