Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated aldehydes

Organic & Biomolecular Chemistry
Shangbin JinWanbin Zhang

Abstract

The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated aldehydes has been presented. The new organocatalyst readily facilitates the enantioselective alkylation reaction, providing 3-alkylated indoles in good to high yields (62-89%) with high levels of enantioselectivity (80-93% ee) using only 2 mol% of catalyst loading.

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