Gold-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions or in Water
Authors:
- 14 September 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (21) , 4323-4326
Abstract
A gold(III)-catalyzed multicomponent coupling/cycloisomerization reaction of heteroaryl aldehydes, amines, and alkynes under solvent-free conditions or in water has been developed. This methodology provides rapid access to substituted aminoindolizines with high atom economy and high catalytic efficiency. Especially, the coupling of enantiomerically enriched amino acid derivatives produces the corresponding N-indolizine-incorporated amino acid derivatives without loss of enantiomeric purity.Keywords
This publication has 29 references indexed in Scilit:
- Pt-Catalyzed Cyclization/1,2-Migration for the Synthesis of Indolizines, Pyrrolones, and IndolizinonesOrganic Letters, 2007
- Gold-Catalyzed 1,2-Migration of Silicon, Tin, and Germanium en Route to C-2 Substituted Fused Pyrrole-Containing HeterocyclesJournal of the American Chemical Society, 2006
- A Novel Coupling 1,3‐Dipolar Cycloaddition Sequence as a Three‐Component Approach to Highly Fluorescent IndolizinesHelvetica Chimica Acta, 2005
- Selective Partial Reduction of Various Heteroaromatic Compounds with Bridgehead Nitrogen via Birch Reduction ProtocolThe Journal of Organic Chemistry, 2005
- Highly Diastereoselective Approach toward (±)-Tetraponerine T6 and Analogues via the Double Cycloisomerization−Reduction of Bis-alkynylpyrimidinesThe Journal of Organic Chemistry, 2004
- Double Cycloisomerization as a Novel and Expeditious Route to Tricyclic Heteroaromatic Compounds: Short and Highly Diastereoselective Synthesis of (±)-Tetraponerine T6Organic Letters, 2002
- A Novel Cu-Assisted Cycloisomerization of Alkynyl Imines: Efficient Synthesis of Pyrroles and Pyrrole-Containing HeterocyclesJournal of the American Chemical Society, 2001
- Organic reactions in aqueous media - with a focus on carbon-carbon bond formationChemical Reviews, 1993
- Multicomponent one-pot annulations forming 3 to 6 bondsChemical Reviews, 1986
- One-step Synthesis of 3-(Dialkylamino)indolizines by the Palladium-catalyzed Reaction of α-Bromopyridine, Propargyl Alcohol, and Secondary AmineBulletin of the Chemical Society of Japan, 1980