Organocatalytic Three‐Component Reactions of Pyruvate, Aldehyde and Aniline by Hydrogen‐Bonding Catalysts
Authors:
- 19 August 2008
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2008 (25) , 4350-4356
Abstract
Hydrogen‐bonding catalysts have been found to catalyze one‐pot three‐component reactions of pyruvate, anilines and aldehydes to afford versatile 3‐amino‐1,5‐dihydro‐2H‐pyrrol‐2‐ones in high yields. Both, thioureas and phosphoric acids are viable catalysts for these reactions and have comparable activity. The corresponding chiral thioureas and phosphoric acids have also been used in these three‐component reactions to give pyrrol‐2‐ones in high yields and with moderate enantioselectivities.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)Keywords
This publication has 58 references indexed in Scilit:
- Organocatalytic Asymmetric Three‐Component Cyclization of Cinnamaldehydes and Primary Amines with 1,3‐Dicarbonyl Compounds: Straightforward Access to Enantiomerically Enriched DihydropyridinesAngewandte Chemie International Edition, 2008
- Catalytic Enantioselective Passerini Three‐Component ReactionAngewandte Chemie International Edition, 2007
- Chiral Salen−Aluminum Complex as a Catalyst for Enantioselective α-Addition of Isocyanides to Aldehydes: Asymmetric Synthesis of 2-(1-Hydroxyalkyl)-5-aminooxazolesOrganic Letters, 2007
- Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich ReactionJournal of the American Chemical Society, 2007
- Enantioselective Direct Aza Hetero-Diels−Alder Reaction Catalyzed by Chiral Brønsted AcidsOrganic Letters, 2006
- Highly Enantioselective Organocatalytic Biginelli ReactionJournal of the American Chemical Society, 2006
- Highly Enantioseletive Biginelli Reaction Using a New Chiral Ytterbium Catalyst: Asymmetric Synthesis of DihydropyrimidinesJournal of the American Chemical Society, 2005
- Multicomponent Reactions2005
- Synthesis and biological activity of 1,5-diaryl-3-arylamino-4-carboxymethyl-2,5-dihydro-2-pyrrolones and 1,5-diaryl-4-carboxymethyltetrahydropyrrole-2, 3-dionesPharmaceutical Chemistry Journal, 1993
- 1,5-Diaryl-2,3-pyrrolidinediones. XII. Enamines and the Pseudo-pyrrolidinediones1,2Journal of the American Chemical Society, 1960