Cinchona alkaloid amide catalyzed enantioselective formal [2+2] cycloadditions of allenoates and imines: synthesis of 2,4-disubstituted azetidines
| Autor: | J. M. Denis, Géraldine Masson, Pascal Retailleau, Jieping Zhu |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Cinchona Alkaloids
Cinchona 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Amide Organic chemistry Alkyl ComputingMilieux_MISCELLANEOUS chemistry.chemical_classification biology Molecular Structure 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Alkaloid Enantioselective synthesis Stereoisomerism General Medicine General Chemistry biology.organism_classification Amides Cycloaddition 0104 chemical sciences 3. Good health Alkadienes chemistry Organocatalysis Azetidines Imines |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie International Edition, Wiley-VCH Verlag, 2011, 50 (23), pp.5356-5360. ⟨10.1002/anie.201100706⟩ |
| ISSN: | 1433-7851 1521-3773 |
| DOI: | 10.1002/anie.201100706⟩ |
| Popis: | Mix and go. The quinidine-amide (1)-catalyzed [2+2] cycloaddition between N-sulfonylimines (2) and alkyl 2,3-butadienoate (3) afforded the (R)-azetidines 4 in excellent yields and enantioselectivities. The (S)-enantiomer was obtained when a quinine-amide catalyst, the pseudoenantiomer of (1) was used. |
| Databáze: | OpenAIRE |
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