Organocatalytic Conjugate Addition of Nitroalkanes to 3-Ylidene Oxindoles: A Stereocontrolled Diversity Oriented Route to Oxindole Derivatives
| Autor: | Claudio Trombini, Marco Lombardo, Elisa Montroni, Arianna Quintavalla, Francesco Lanza |
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| Přispěvatelé: | Arianna Quintavalla, Francesco Lanza, Elisa Montroni, Marco Lombardo, Claudio Trombini |
| Rok vydání: | 2013 |
| Předmět: |
Indoles
Stereochemistry SPIROOXINDOLE DERIVATIVES CARBON QUATERNARY STEREOCENTERS 3-SUBSTITUTED OXINDOLES 3'-DISUBSTITUTED OXINDOLES DIELS-ALDER Catalysis Stereocenter chemistry.chemical_compound NATURAL-PRODUCTS Alkanes Oxindole Bifunctional Molecular Structure ASYMMETRIC MICHAEL Organic Chemistry Thiourea Enantioselective synthesis MULTIPLE STEREOCENTERS Stereoisomerism Nitro Compounds CATALYTIC ENANTIOSELECTIVE CONSTRUCTION chemistry BIFUNCTIONAL ORGANOCATALYSTS Molecular targets Michael reaction Conjugate |
| Zdroj: | The Journal of Organic Chemistry. 78:12049-12064 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo402099p |
| Popis: | An efficient and highly enantioselective Michael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifunctional organocatalysts. The stereochemistry at C-alpha and C-beta centers is perfectly controlled, and the intermediate C-3 enolate is trapped with a second Michael acceptor. The developed one-pot three-component consecutive reactions generate up to four contiguous stereocenters, including the C-3 all-carbon quaternary center, in a perfectly defined configuration. The conversion of the beta-nitro oxindole into the corresponding beta-amino derivative discloses synthetically useful transformations, exploitable to generate pharmaceutically attractive molecular targets. |
| Databáze: | OpenAIRE |
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