Title:Chiral BrOnsted Acid-Catalyzed Friedel-Crafts Reaction of Indoles
Volume: 18
Issue: 16
Author(s): Pinaki S. Bhadury and Jun Pang
Affiliation:
Keywords:
Asymmetric organocatalysis, BINOL, bioactivity, chiral BrØnsted acids, enantioselectivity, Friedel-Crafts alkylation, hydrogenbond,
indole, synthesis.
Abstract: The indole network has been identified as an important pharmacophore of several natural products and synthetically prepared
molecules. Asymmetric organocatalytic Friedel-Crafts alkylations of electron rich indoles are of enormous significance for the synthesis
of many bioactive compounds, natural products and anti-cancer drugs. Chiral BrOnsted acid-catalyzed Friedel-Crafts-type reactions of
indole and its derivatives with various carbon-centered electrophiles e.g. electron deficient olefins, carbonyls, imines and some substituted
methanamines and carbinols have been employed to prepare optically active indole derivatives. These reactions, their stereochemical
outcome and probable modes of activation of the substrates by suitably substituted axially dissymmetric BINOL-derived chiral BrOnsted
acid catalysts are discussed in this review.
