Pd(OAc)<sub>2</sub>-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

Chen, Jianzhong; Zhang, Zhenfeng; Li, Bowen; Li, Feilong; Wang, Yulin; Zhao, Min; Gridnev, Ilya D; Imamoto, Tsuneo et al. · Nat Commun · 2018

basic_science · Level V

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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 hindered N-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 different S- and R-reaction pathways.