Asymmetric Friedel−Crafts Reaction of Indoles with Imines by an Organic Catalyst
Top Cited Papers
- 1 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (25), 8156-8157
- https://doi.org/10.1021/ja062700v
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.Keywords
This publication has 38 references indexed in Scilit:
- The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino AcidsJournal of the American Chemical Society, 2006
- Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivativeChemical Communications, 2006
- Catalytic Asymmetric Pictet−Spengler ReactionJournal of the American Chemical Society, 2006
- Catalytic Enantioselective Friedel–Crafts Alkylation of Indoles with Nitroalkenes by Using a Simple Thiourea OrganocatalystAngewandte Chemie, 2005
- Catalytic Enantioselective C−C Bond Forming Conjugate Additions with Vinyl SulfonesJournal of the American Chemical Society, 2005
- New Catalytic Approaches in the Stereoselective Friedel–Crafts Alkylation ReactionAngewandte Chemie, 2004
- Marine natural productsNatural Product Reports, 2001
- Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino Acid N-CarboxyanhydridesJournal of the American Chemical Society, 2001
- Biphenylphosphine-Palladium(II) Complexes-Catalyzed Friedel-Crafts Reaction for the Synthesis of α-Amino and α-Hydroxy Indolylacetates and DiindolylacetatesSynlett, 2001
- Enantioselective conversion of anthranilic acid derivatives to chiral cyclohexanes. Total synthesis of (+)-pumiliotoxin CJournal of the American Chemical Society, 1987