Practical Highly Enantioselective Synthesis of Propargylamines through a Copper‐Catalyzed One‐Pot Three‐Component Condensation Reaction
- 17 May 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (16) , 4380-4392
- https://doi.org/10.1002/chem.200501233
Abstract
The one-pot three-component reaction of terminal alkynes, aldehydes and secondary amines in the presence of copper(I) bromide/quinap is reported. The reaction scope has been determined and a broad variety of all three components has been used, which afforded the corresponding propargylamines in good to excellent yields and moderate to very good enantioselectivities. The reaction showed a strong positive nonlinear effect. The transformation of a propargylamine intermediate into the alkaloid (S)-(+)-coniine has also been described.Keywords
This publication has 65 references indexed in Scilit:
- A Novel Microwave-Mediated One-Pot Synthesis of Indolizines via a Three-Component ReactionOrganic Letters, 2003
- The Development of a Catalytic Synthesis of Münchnones: A Simple Four-Component Coupling Approach to α-Amino Acid DerivativesJournal of the American Chemical Society, 2003
- One-Pot Three-Component Reaction for the Synthesis of α-(Aminoethyl)-α,β-enonesOrganic Letters, 2002
- InCl3-Catalyzed Three-Component Asymmetric Mannich-Type Reaction in MethanolOrganic Letters, 2002
- Synthesis of Allyl Cyanamides and N-Cyanoindoles via the Palladium-Catalyzed Three-Component Coupling ReactionJournal of the American Chemical Society, 2002
- A Novel Titanium Tetrahalide-Mediated Carbon−Carbon Bond-Forming Reaction: Regioselective Synthesis of Substituted (E,Z)-1,5-Dihalo-1,4-dienesOrganic Letters, 2002
- The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction: Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino AlcoholsJournal of the American Chemical Society, 2002
- Novel Synthetic Route to Allyl Cyanamides: Palladium-Catalyzed Coupling of Isocyanides, Allyl Carbonate, and Trimethylsilyl AzideJournal of the American Chemical Society, 2001
- Multikomponentenreaktionen mit IsocyanidenAngewandte Chemie, 2000
- Multicomponent Reactions with IsocyanidesPublished by Wiley ,2000