Three-Component Domino Knoevenagel/Hetero-Diels-Alder Reaction for the Synthesis of the Amino Sugars 2-Acetoxyforosamine and 2-Acetoxyossamine - Experimental and Theoretical Results
| Autor: | Lutz F. Tietze, Niels Böhnke, M. Alexander Düfert, Simone Dietz, Dietmar Stalke, Ina Objartel |
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| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_classification
Reaction mechanism Double bond 010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Reductive amination Cycloaddition Domino 3. Good health 0104 chemical sciences chemistry Nitro Organic chemistry Knoevenagel condensation Physical and Theoretical Chemistry Diels–Alder reaction |
| Zdroj: | European Journal of Organic Chemistry. 2011:6574-6580 |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201100725 |
| Popis: | The three-component domino Knoevenagel/hetero-Diels–Alder reaction of nitroacetone (6), formaldehyde and ethoxyvinylacetate (4) leads to dihydropyrans 10 and 11, which after hydrogenation of the double bond as well as consecutive reduction of the nitro group and reductive amination give the desired forosamine-type 2-acetoxyamino sugars 21–24 and ossamine-type 25. |
| Databáze: | OpenAIRE |
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