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Org Lett. 2019 May 17;21(10):3682-3686. doi: 10.1021/acs.orglett.9b01127. Epub 2019 May 1.

Design of Planar Chiral Phosphoric Acids with a [2.2]Paracyclophanyl Backbone as Organocatalysts for the Highly Enantioselective Aza-Friedel-Crafts Reaction.

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1
Department of Chemistry , Zhejiang University , Hangzhou 310027 , China.

Abstract

A new type of robust planar chiral phosphoric acid bearing a [2.2]paracyclophane scaffold was synthesized and shown to be an optimal catalyst in asymmetric aza-Friedel-Crafts reactions for the first synthesis of enantioenriched styryl indolylmethanamine derivatives in good yields with excellent enantioselectivities (93->99% ee) under 0.5-1 mol % catalyst loading.

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