Exploration of a Novel, Enamine-Solid-Base Catalyzed Aldol Condensation with C-Glycosidic Pyranoses and Furanoses
| Autor: | Julien Hitce, Philip Coish, Yanna Balland, Tamara M. de Winter, Arwen Evenstar Neski, Julie B. Zimmerman, Laurène Petitjean, Magali Moreau, Paul T. Anastas, Hanno C. Erythropel |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Renewable Energy Sustainability and the Environment Magnesium organic chemicals General Chemical Engineering chemistry.chemical_element Glycosidic bond General Chemistry 010402 general chemistry Heterogeneous catalysis 01 natural sciences 0104 chemical sciences Enamine Catalysis chemistry.chemical_compound chemistry Aldol reaction Environmental Chemistry Organic chemistry Knoevenagel condensation Aldol condensation |
| Zdroj: | ACS Sustainable Chemistry & Engineering. 6:11196-11199 |
| ISSN: | 2168-0485 |
| Popis: | A variety of unprotected C-glycosidic ketones were employed in a novel enamine-solid-base catalyzed (ESBC) aldol condensation to expand the scope and scalability of a previously reported reaction. The starting ketones were obtained from unprotected pyranoses and furanoses following Lubineau’s method via a Knoevenagel condensation. The aldol condensation reaction of the C-glycosidic ketones was performed with a nontoxic and abundant amino acid, L-proline, along with magnesium oxide (MgO) as a recyclable and sustainable catalyst. The enamine-solid-base catalyzed aldol condensations provided the corresponding (E)-α,β-unsaturated ketones in excellent isolated yields (91–100%). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|