Dinuclear zinc catalyzed asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines?

Organic & Biomolecular Chemistry Pub Date: 2011-02-14 DOI: 10.1039/C0OB01200A

Abstract

The asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85–98%) with moderate to high enantiomeric ratios (from 70?:?30 up to 95?:?5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl methanamines, which avoids the formation of the undesirable bis- and tris(indolyl)methanes (BIMs and TIMs) byproduct.

Graphical abstract: Dinuclear zinc catalyzed asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines
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