Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids

Molecules

Arrigo Scettri²  Rosaria Villano¹ 

[1] Istituto di Chimica Biomolecolare-CNR Trav. La Crucca3, Reg. Baldinca 07040, Li Punti, Sassari, Italy; E-mail:;Dipartimento di Chimica, Università di Salerno, Via Ponte Don Melillo 84084, Fisciano, Salerno, Italy; E-mail:

关键词: asymmetric Friedel-Crafts;    indole;    chiral phosphoric acids;   

DOI  :  10.3390/molecules14083030

来源: mdpi

【 摘 要 】

The reaction of indole with chalcones, to give Michael-type adducts, was found to occur with good efficiency (up to 98% yield) and moderate enantioselectivity (up to 52% e.e.) in the presence of a chiral BINOL-based phosphoric acid. Furthermore, the alkylation products can be obtained in much higher e.e.s after one only crystallization.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.