Enantioselective Michael reaction of nitroalkanes onto nitroalkenes catalyzed by cinchona alkaloid derivatives
| Autor: | Zhen-Wei Zhang, Yan-Qiu Deng, Ya-Hui Feng, Gui Lu, Albert S. C. Chan |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
biology
010405 organic chemistry Alkaloid Organic Chemistry Enantioselective synthesis Cinchona 010402 general chemistry biology.organism_classification 01 natural sciences Asymmetric induction Catalysis 0104 chemical sciences 3. Good health Inorganic Chemistry Reaction rate chemistry.chemical_compound chemistry Nitroethane Michael reaction Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Tetrahedron: Asymmetry; Vol 23 |
| ISSN: | 0957-4166 |
| Popis: | An effective asymmetric synthesis of optically active 1,3-dinitro compounds via the direct Michael addition of nitroalkanes onto nitroalkenes has been described. In the presence of readily modified cinchona alkaloid derivatives, nitroethane reacted well with a variety of aromatic and heterocyclic aromatic nitroalkenes to afford products with good diastereoselectivities (dr up to 72/28) and enantioselectivities (ee up to 94%). The catalyst loading can be decreased to 2 mol % without compromising the asymmetric induction or the reaction rate. |
| Databáze: | OpenAIRE |
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