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Pd(OAc)₂-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

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.

SUBMITTER: Chen J

PROVIDER: S-EPMC6258694 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

Chen Jianzhong J Zhang Zhenfeng Z Li Bowen B Li Feilong F Wang Yulin Y Zhao Min M Gridnev Ilya D ID Imamoto Tsuneo T Zhang Wanbin W

Nature communications 20181127 1

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 d ...[more]

PMID: 30479338

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