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

doi:10.1016/S1872-2067(17)62804-3

Abstract

Abstract:

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.

Key words: Friedel–Crafts reaction, Quaternary α-aminophosphonate, Indole, Chiral phosphoric acid

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.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(17)62804-3

https://www.cjcatal.com/EN/Y2017/V38/I5/784

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