The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes
Top Cited Papers
- 12 June 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (27) , 7894-7895
- https://doi.org/10.1021/ja025981p
Abstract
The first enantioselective organocatalytic alkylation of electron-rich benzene rings with α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and medicinal agent synthesis. The (2S,5S)-5-benzyl-2-tert-butylimidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted anilines to unsaturated aldehydes. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 10 mol % were generally employed in this study, successful alkylations conducted with catalyst loadings as low as 1 mol % are described.Keywords
This publication has 12 references indexed in Scilit:
- Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids and Their Derivatives to Electron Deficient OlefinsSynlett, 2001
- Palladium-Catalyzed α-Arylation of Esters and Protected Amino AcidsJournal of the American Chemical Society, 2001
- Review of sertraline and its clinical applications in psychiatric disordersExpert Opinion on Pharmacotherapy, 2001
- New Strategies in Organic Catalysis: The First Enantioselective Organocatalytic Friedel−Crafts AlkylationJournal of the American Chemical Society, 2001
- Catalytic Enantioselective Friedel−Crafts Reactions of Aromatic Compounds with Glyoxylate: A Simple Procedure for the Synthesis of Optically Active Aromatic Mandelic Acid EstersJournal of the American Chemical Society, 2000
- New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder ReactionJournal of the American Chemical Society, 2000
- Paroxetine: a review of its pharmacology, pharmacokinetics and utility in the treatment of a variety of psychiatric disordersExpert Opinion on Investigational Drugs, 1999
- Rhodium-catalyzed asymmetric 1,4-addition of 2-alkenyl-1,3,2-benzodioxaboroles to α,β-unsaturated ketonesTetrahedron Letters, 1998
- Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to EnonesJournal of the American Chemical Society, 1998
- TolterodineDrugs, 1998