Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines. Issue 1 (December 2018)

• Record Type: Journal Article
• Authors: Chen, Jianzhong; Zhang, Zhenfeng; Li, Bowen; Li, Feilong; Wang, Yulin; Zhao, Min; Gridnev, Ilya; Imamoto, Tsuneo; Zhang, Wanbin
• Is Part Of: Nature communications. Volume 9:Issue 1(2018)
• Page Start: 1
• Page End: 10
• Publication Date: 2018-12
• Subjects: Biology -- Periodicals; Physical sciences -- Periodicals; 505
• DOI: 10.1038/s41467-018-07462-w
• Languages: English
• ISSNs: 2041-1723

Abstract

Abstract Asymmetric hydrogenation of sterically hindered substrates still constitutes a long-standing challenge in the area of asymmetric catalysis. Herein, an efficient palladium acetate (an inexpensive Pd salt with low toxicity) catalyzed asymmetric hydrogenation of sterically hinderedN -tosylimines is realized with high catalytic activities (S/C up to 5000) and excellent enantioselectivities (ee up to 99.9%). Quantum chemical calculations suggest that uniformly high enantioselectivities are observed due to the structurally differentS - andR- reaction pathways. Sterically hindered unsaturated compounds are challenging substrates for asymmetric hydrogenation. Here, the authors report a palladium/chiral (bis)phosphine catalytic system that hydrogenates a number of hinderedN -tosylimines with excellent enantioselectivitites.