α,β-Unsaturated Acyl Cyanides as New Bis-Electrophiles for Enantioselective Organocatalyzed Formal [3+3]Spiroannulation
| Autor: | Xavier Bugaut, Sébastien Goudedranche, Jean Rodriguez, Thierry Constantieux, Damien Bonne |
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| Přispěvatelé: | Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), ANR-11-BS07-0014,OEREKA,Réactions Enantiosélectives Organocatalysées à partir de Cétoamides(2011), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2013 |
| Předmět: |
[CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry Stereochemistry Chemistry domino reactions Organic Chemistry spiroannulation Enantioselective synthesis General Chemistry Optically active 010402 general chemistry Ring (chemistry) 01 natural sciences Catalysis Domino 0104 chemical sciences Acylation Organocatalysis enantioselectivity Electrophile organocatalysis Reactivity (chemistry) glutarimides |
| Zdroj: | Chemistry-A European Journal Chemistry-A European Journal, Wiley-VCH Verlag, 2014, 20 (2), pp.410-415. ⟨10.1002/chem.201303613⟩ Chemistry-A European Journal, 2014, 20 (2), pp.410-415. ⟨10.1002/chem.201303613⟩ |
| ISSN: | 0947-6539 1521-3765 |
| DOI: | 10.1002/chem.201303613 |
| Popis: | International audience; α,β-Unsaturated acyl cyanides are key bis-electrophile substrates for successful domino enantioselective organocatalyzed Michael-intramolecular acylation domino sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4,5]decanone ring systems by a formal [3+3]spiroannulation, constituting a rare example of synthesis of glutarimides in an optically active form. |
| Databáze: | OpenAIRE |
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