Transition Metal Salt-Catalyzed Direct Three-Component Mannich Reactions of Aldehydes, Ketones, and Carbamates: Efficient Synthesis of N-Protected β-Aryl-β-Amino Ketone Compounds
- 30 October 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (24) , 8482-8484
- https://doi.org/10.1021/jo048778g
Abstract
The transition metal salt-catalyzed direct three-component Mannich reactions of aryl aldehydes, aryl ketones, and carbamates are described. The RuCl(3).xH(2)O-, AuCl(3)-PPh(3)-, and AuCl(3)-catalyzed direct Mannich reactions led to the synthesis of N-protected beta-aryl-beta-amino ketones, and the results create new possibilities for exploiting the transition metal salt-catalyzed direct Mannich reaction and facile synthesis of beta-amino ketone libraries.Keywords
This publication has 44 references indexed in Scilit:
- Gold‐Catalyzed Hydroarylation of AlkynesEuropean Journal of Organic Chemistry, 2003
- A Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amines via C−H Activation Catalyzed by Gold in WaterJournal of the American Chemical Society, 2003
- Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalystChemical Communications, 2003
- Montmorillonite K10 Clay: An Efficient Catalyst for the One-Pot Stereoselective Synthesis of β-Acetamido KetonesThe Journal of Organic Chemistry, 2003
- Direct Catalytic Asymmetric Mannich Reactions of Malonates and β‐Keto EstersChemistry – A European Journal, 2003
- Diastereoselective Addition of Chlorotitanium Enolate of N-Acyl Thiazolidinethione to O-Methyl Oximes: A Novel, Stereoselective Synthesis of α,β-Disubstituted β-Amino Carbonyl Compounds via Chiral Auxiliary Mediated Azetine FormationJournal of the American Chemical Society, 2003
- Via Ugi reactions to conformationally fixed cyclic peptidesDedicated to Professor Dr D. Seebach on the occasion of his 65th birthday.Chemical Communications, 2003
- Green Chemistry Approaches to the Synthesis of 5-Alkoxycarbonyl-4-aryl-3,4- dihydropyrimidin-2(1H)-ones by a Three-Component Coupling of One-Pot Condensation Reaction: Comparison of Ethanol, Water, and Solvent-free ConditionsThe Journal of Organic Chemistry, 2002
- Gold(I)-Catalyzed Asymmetric Aldol Reaction of N-Methoxy-N-methyl-.alpha.-isocyanoacetamide (.alpha.-Isocyano Weinreb Amide). An Efficient Synthesis of Optically Active .beta.-Hydroxy .alpha.-Amino Aldehydes and KetonesThe Journal of Organic Chemistry, 1995
- Preparation of 2,3,4,5-Tetrahydropyridines from 5-Alkynylamines Under the Catalytic Action of Gold(III) SaltsSynthesis, 1991