Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst
Yong-Qiang Wang1, Jun Song, Ran Hong
1Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Abstract:
In this communication, we report an asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst. This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines. This reaction is operationally simple and, unprecedentedly, affords high enantioselectivity for a wide range of indoles and both aryl and alkyl imines. This establishes a direct, convergent, and versatile approach to optically active 3-indolyl methanamines, a structural motif embedded in numerous indole alkaloids and synthetic indole derivatives.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Limitations of Friedel–Crafts Reactions
Amines to Alkenes: Hofmann Elimination
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation


