Asymmetric Organocatalytic Friedel–Crafts Hydroxyalkylation of Indoles Using Electrophilic Pyrazole-4,5-diones

Abstract

The electrophilic reactivity of a series of novel pyrazole-4,5-dione derivatives in the organocatalytic Friedel–Crafts reaction with various substituted indoles has been tested. The disclosed procedure catalyzed by a cinchona alkaloid derivative allows the conjugation of two very important aza-heterocyclic scaffolds to generate a new class of indolylpyrazolones bearing a tetrasubstituted stereocenter in excellent yields (up to 99%) and with enantioselectivities of up to 94:6 er.

Key words

Friedel–Crafts - organocatalysis - pyrazolones - indoles - tetrasubstituted­ stereocenter

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