Brønsted Acid Catalyzed Propargylation of 1,3-Dicarbonyl Derivatives. Synthesis of Tetrasubstituted Furans
- 27 January 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (4), 727-730
- https://doi.org/10.1021/ol0631298
Abstract
Simple Brønsted acids such as p-toluenesulfonic acid monohydrate (PTS) efficiently catalyze a direct substitution of the hydroxyl group in propargylic alcohols with 1,3-dicarbonyl compounds. Selective propargylation or allenylation is obtained depending on the nature of the alkynol. Reactions can be performed in air in undried solvents with water being the only side product of the process. By applying this reaction as the key step, a range of interesting polysubstituted furans can easily be synthesized in a one-pot procedure. [reaction: see text].Keywords
This publication has 14 references indexed in Scilit:
- Brønsted Acid‐Catalyzed Nucleophilic Substitution of AlcoholsAdvanced Synthesis & Catalysis, 2006
- BiCl3-Catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophilesChemical Communications, 2006
- Brønsted Acid Mediated Heterogeneous Addition Reaction of 1,3‐Dicarbonyl Compounds to Alkenes and AlcoholsAngewandte Chemie International Edition, 2006
- Chiral 3D Architectures with Helical Channels Constructed from Polyoxometalate Clusters and Copper–Amino Acid ComplexesAngewandte Chemie International Edition, 2006
- Preparation of Dicationic Chalcogenolate-Bridged Diruthenium Complexes and Their Dual Catalytic Activity toward Reactions between Propargylic Alcohols and AcetoneOrganometallics, 2005
- Gold(III)-Catalyzed Nucleophilic Substitution of Propargylic AlcoholsJournal of the American Chemical Society, 2005
- A Re(V)-Catalyzed C−N Bond-Forming Route to Human Lipoxygenase InhibitorsOrganic Letters, 2005
- Ruthenium‐Catalyzed Propargylic Substitution Reactions of Propargylic Alcohols with Oxygen‐, Nitrogen‐, and Phosphorus‐Centered NucleophilesChemistry – A European Journal, 2005
- On Inventing Reactions for Atom EconomyAccounts of Chemical Research, 2002
- Ruthenium-Catalyzed Propargylic Alkylation of Propargylic Alcohols with Ketones: Straightforward Synthesis of γ-Keto AcetylenesJournal of the American Chemical Society, 2001