Redox-Triggered CC Coupling of Diols and Alkynes: Synthesis of β,γ-Unsaturated α-Hydroxyketones and Furans by Ruthenium-Catalyzed Hydrohydroxyalkylation
| Autor: | Emma L. McInturff, Khoa D. Nguyen, Michael J. Krische |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure Alkene chemistry.chemical_element Regioselectivity Stereoisomerism General Medicine General Chemistry Ketones Transfer hydrogenation Medicinal chemistry Redox Ruthenium Article Catalysis chemistry Cyclization Alkynes Reagent Organic chemistry Furans Oxidation-Reduction |
| Zdroj: | Angewandte Chemie International Edition. 53:3232-3235 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201311130 |
| Popis: | Direct ruthenium-catalyzed CC coupling of alkynes and vicinal diols to form β,γ-unsaturated ketones occurs with complete levels of regioselectivity and good to complete control over the alkene geometry. Exposure of the reaction products to substoichiometric quantities of p-toluenesulfonic acid induces cyclodehydration to form tetrasubstituted furans. These alkyne-diol hydrohydroxyalkylations contribute to a growing body of merged redox-construction events that bypass the use of premetalated reagents and, hence, stoichiometric quantities of metallic by-products. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text