Asymmetric C-alkylation with chiral phase-transfer catalysis. Synthesis of optically active derivatives of 2-indolinone was written by Chen, Banghua;Ji, Qinge. And the article was included in Huaxue Xuebao in 1989.Formula: C26H29ClN2O This article mentions the following:
By using different chiral quaternary ammonium salts as phase-transfer catalysts, the asym. C-alkylation of 1,3-dimethyl-5-methoxy-2-indolinone with various alkyl bromides is carried out. The effects of the catalysts, alkylating agents, solvents, and reaction temperatures on the optical activity of the products are studied. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Formula: C26H29ClN2O).
(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%–96%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).Formula: C26H29ClN2O
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider