Unexpected change of absolute configuration in asymmetric Michael addition of methyl vinyl ketone to 2-nitrocycloalkanones
| Autor: | Anthony Linden, Manfred Hesse, Anita Latvala, Stephan Stanchev |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
Diketone
chemistry.chemical_classification Ketone Chemistry Organic Chemistry Absolute configuration Cinchonine Medicinal chemistry Catalysis Inorganic Chemistry Ring size chemistry.chemical_compound Methyl vinyl ketone Michael reaction Organic chemistry Physical and Theoretical Chemistry Enantiomeric excess |
| Zdroj: | Tetrahedron: Asymmetry. 4:173-176 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/s0957-4166(00)82330-7 |
| Popis: | Michael addition of methyl vinyl ketone 2 to 2-nitrocycloalkanones 1 catalyzed by the Cinchona alkaloid cinchonine 3 affords adducts in high chemical yields in up to 60% enantiomeric excess. The configuration of the products depends on the ring size. Absolute configuration of (−)-2-nitro-2-(3-oxobutyl)cyclooctanone and (+)-2-nitro-2-(3-oxobutyl)cyclododecanone derivatives were determined by X-ray diffraction. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|