Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light
Lu Lin
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
These authors contributed equally to this work.
Search for more papers by this authorXiangbin Bai
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
These authors contributed equally to this work.
Search for more papers by this authorXinyi Ye
Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore
Search for more papers by this authorXiaowei Zhao
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
Search for more papers by this authorProf. Dr. Choon-Hong Tan
Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhiyong Jiang
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
Search for more papers by this authorLu Lin
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
These authors contributed equally to this work.
Search for more papers by this authorXiangbin Bai
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
These authors contributed equally to this work.
Search for more papers by this authorXinyi Ye
Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore
Search for more papers by this authorXiaowei Zhao
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
Search for more papers by this authorProf. Dr. Choon-Hong Tan
Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhiyong Jiang
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 P.R. China
Search for more papers by this authorGraphical Abstract
Enantioselective protonation: The first catalytic asymmetric photoreduction of 1,2-diketones and α-keto ketimines under visible light irradiation relies on a transition-metal-free cooperative catalysis platform that harnesses dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst and a noncovalent chiral organocatalyst. A variety of chiral α-hydroxy ketones and α-amino ketones was obtained with high yields and enantioselectivities.
Abstract
The first catalytic asymmetric photoreduction of 1,2-diketones and α-keto ketimines under visible light irradiation is reported. A transition-metal-free synergistic catalysis platform harnessing dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst and a non-covalent chiral organocatalyst is effective for these transformations. With the flexible use of a chiral Brønsted acid or base in H+ transfer interchange to control the elusive enantioselective protonation, a variety of chiral α-hydroxy ketones and α-amino ketones were obtained with high yields and enantioselectivities.
Supporting Information
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