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. © Georg Thieme Verlag Stuttgart. New York.
Asymmetric oganocatalytic Friedel-Crafts hydroxyalkylation of indoles using electrophilic pyrazole-4,5-diones / Vetica, Fabrizio; Chauhan, Pankaj; Mahajan, Suruchi; Raabe, Gerhard; Enders, Dieter. - In: SYNTHESIS. - ISSN 0039-7881. - 50:5(2018), pp. 1039-1046. [10.1055/s-0036-1591860]
Asymmetric oganocatalytic Friedel-Crafts hydroxyalkylation of indoles using electrophilic pyrazole-4,5-diones
Vetica, Fabrizio;
2018
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. © Georg Thieme Verlag Stuttgart. New York.| File | Dimensione | Formato | |
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