Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis
Dong-Huang Chen
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
These authors contributed equally to this work.
Search for more papers by this authorWei-Ting Sun
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
These authors contributed equally to this work.
Search for more papers by this authorCheng-Jie Zhu
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
These authors contributed equally to this work.
Search for more papers by this authorGuang-Sheng Lu
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
Search for more papers by this authorDong-Ping Wu
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
Search for more papers by this authorCorresponding Author
Dr. Ai-E Wang
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, Gansu China
Search for more papers by this authorCorresponding Author
Prof. Dr. Pei-Qiang Huang
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, Gansu China
Search for more papers by this authorDong-Huang Chen
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
These authors contributed equally to this work.
Search for more papers by this authorWei-Ting Sun
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
These authors contributed equally to this work.
Search for more papers by this authorCheng-Jie Zhu
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
These authors contributed equally to this work.
Search for more papers by this authorGuang-Sheng Lu
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
Search for more papers by this authorDong-Ping Wu
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
Search for more papers by this authorCorresponding Author
Dr. Ai-E Wang
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, Gansu China
Search for more papers by this authorCorresponding Author
Prof. Dr. Pei-Qiang Huang
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, Gansu China
Search for more papers by this authorGraphical Abstract
The first enantioselective reductive cyanation and phosphonylation of secondary amides have been achieved by the combination of iridium with chiral thiourea catalysis. The protocol is highly efficient and enantioselective, providing a novel route for the synthesis of optically active α-aminonitriles and α-aminophosphonates from bench-stable feedstocks.
Abstract
The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.
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