24802-69-5Relevant academic research and scientific papers
Ruthenium-Catalyzed Highly Enantioselective Synthesis of cis-3-Quinuclidinols via DKR Asymmetric Transfer Hydrogenation
Luo, Zhonghua,Wang, Zhongqing,Sun, Guodong,Jian, Weilin,Jiang, Fengkai,Luan, Baolei,Li, Ridong,Zhang, Lei
, p. 4322 - 4326 (2020/06/04)
A method for the enantioselective synthesis of cis-3-quinuclidinols by Ru-catalyzed asymmetric transfer hydrogenation via dynamic kinetic resolution is described. The reaction proceeded under mild conditions using ammonium formate as the hydrogen donor, affording the products in high yields (up to 99%) with excellent diastereoselectivity (up to 99:1 dr) and enantioselectivity (95-99% ee). This protocol was applicable to gram-scale preparation with perfect enantioselectivity through simple recrystallization.
Quinuclidine chemistry. 2. Synthesis and antiinflammatory properties of 2 substituted benzhydryl 3 quinuclidinols
Warawa,Mueller,Jules
, p. 497 - 501 (2007/10/05)
A number of 2 benzhydryl 3 quinuclidinols were tested for their anti inflammatory activity. The cis isomers were prepared selectively by aluminum isopropoxide reduction of the ketones which were made by the addition of aromatic Grignard reagents to 2 benzylidene 3 quinuclidinones. The most active compound was cis 2 (4,4' difluorobenzhydryl) 3 quinuclidinol. The trans alcohol was less active than the cis isomer. It was made by selectively oxidizing the cis alcohol in a mixture of cis and trans alcohols (formed by NaBH4 reduction of the ketone) followed by chromatography. The two diastereoisomers of the monofluorinated alcohol, 2 (4 fluorobenzhydryl) 3 quinuclidinol, showed activity but were markedly less active than the difluorinated alcohol. The quinuclidine nitrogen was vital for activity for cis 3 (4,4 difluorobenzhydryl) bicyclo [2.2.2] octan 2 one showed only marginal activity.
