Azole‐Directed Cobalt‐Catalyzed Asymmetric Hydrogenation of Alkenes. Issue 44 (20th June 2022)

• Record Type: Journal Article
• Authors: Jin, Yue; Zou, Yashi; Hu, Yanhua; Han, Yunxi; Zhang, Zhenfeng; Zhang, Wanbin
• Is Part Of: Chemistry. Volume 28:Issue 44(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-20
• Subjects: alkenes -- asymmetric hydrogenation -- azoles -- bisphosphines -- cobalt; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201517
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The azole‐directed cobalt‐catalyzed asymmetric hydrogenation of alkenes has been developed with high efficiency. With this approach, chiral pyrazole compounds were obtained in quantitative yields and excellent enantioselectivities (up to 99 % ee) under mild conditions, and the hydrogenation was conducted on a gram scale with up to 2000 TON. Several useful applications were demonstrated including the convenient introduction of β‐chirality to a drug intermediate containing an azole ring. Abstract : By the assisting promotion effect of the azolyl group itself, an efficient Co‐catalyzed asymmetric hydrogenation of azolyl‐substituted alkenes has been successfully developed for the convenient introduction of chirality near the azole ring. It was the first utilization of an azole as the directing group in Co‐catalyzed asymmetric hydrogenation. Chiral azoles were obtained in high yields and with excellent enantioselectivities under mild conditions and the gram‐scale experiment went smoothly at up to 2000 substrate/catalyst.