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Protonated Bis-1,2,3-triazole as an Anion-Binding Chiral Brønsted Acid for Catalytic Asymmetric Friedel–Crafts Reaction of Indoles with Imines

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The complex of chiral C2-symmetric bis-1,2,3-triazole and an achiral Bronsted acid is introduced as a new class of chiral acid catalysts. The catalytic activity and stereocontrolling ability of this chiral… Click to show full abstract

The complex of chiral C2-symmetric bis-1,2,3-triazole and an achiral Bronsted acid is introduced as a new class of chiral acid catalysts. The catalytic activity and stereocontrolling ability of this chiral Bronsted acid can be tuned simply by changing the achiral acid. The synthetic relevance of this salient feature is demonstrated in the asymmetric Friedel–Crafts reaction of indoles with N-sulfonyl imines.

Keywords: reaction indoles; asymmetric friedel; crafts reaction; bis triazole; acid; friedel crafts

Journal Title: Bulletin of the Chemical Society of Japan
Year Published: 2018

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