Highly efficient asymmetric organocatalytic Friedel–Crafts alkylation of indoles with α,β-unsaturated aldehydes†,10.1039/C0OB00016G

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Highly efficient asymmetric organocatalytic Friedel–Crafts alkylation of indoles with α,β-unsaturated aldehydes†

Shangbin Jin,Chenguang Li,Yuanhui Ma,Yuhe Kan,Yong Jian Zhang,Wanbin Zhang

Organic & Biomolecular Chemistry Pub Date : 07/09/2010 00:00:00 , DOI:10.1039/C0OB00016G

Abstract

The development of an improved organocatalyst, N-isopropylated bipyrrolidine 2a, for the asymmetric Friedel–Crafts alkylation of indoles with α,β-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.