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Citation: Zhong Yan, Xiang Gao, Yong-Gui Zhou. Enantioselective synthesis of quaternary α-aminophosphonates by organocatalytic Friedel–Crafts reactions of indoles with cyclic α-ketiminophosphonates[J]. Chinese Journal of Catalysis, ;2017, 38(5): 784-792. doi: 10.1016/S1872-2067(17)62804-3 shu

Enantioselective synthesis of quaternary α-aminophosphonates by organocatalytic Friedel–Crafts reactions of indoles with cyclic α-ketiminophosphonates

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received Date: 20 January 2017
Revised Date: 28 February 2017

Fund Project: This work was supported by the National Natural Science Foundation of China (21532006, 21690074).

An efficient asymmetric Friedel–Crafts reaction has been developed for the synthesis of optically active quaternary α-aminophosphonates with up to 98% ee. The synthesis involves the reaction of cyclic α-ketiminophosphonates with indoles using an H8-BINOL-derived chiral phosphoric acid (CPA) catalyst that bears electron-withdrawing 3,5-ditrifluoromethylphenyl substituents on its 3- and 3'-positions. This Friedel–Crafts reaction of cyclic α-ketiminophosphonates was also successful with pyrrole.
- Friedel–Crafts reaction,
- Quaternary α-aminophosphonate,
- Indole,
- Chiral phosphoric acid
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