Diastereoselective cyclocarbonylation of isopulegol by palladium(II) complexes containing no chiral ligands |
| |
| Affiliation: | 1. Institute of Inorganic Chemistry, University of Vienna, Waehringer Strasse 42, 1090 Vienna, Austria;2. Institute of Cancer Research and Comprehensive Cancer Center, Medical University of Vienna, Borschkegasse 8a, 1090 Vienna, Austria;3. Research Platform “Translational Cancer Therapy Research”, University of Vienna and Medical University of Vienna, Vienna, Austria;4. Institute of Analytical Chemistry, University of Vienna, Waehringer Strasse 38, 1090 Vienna, Austria;5. Institute of Pharmacology and Toxicology, Department of Biomedical Sciences, University of Veterinary Medicine Vienna, Veterinaerplatz 1, 1210 Vienna, Austria |
| |
| Abstract: | The cyclocarbonylation of isopulegol catalyzed by palladium(II) complexes containing no chiral ligands produces the two compounds (1R,5R or 5S,6S,9R)-5,9-dimethyl-2-oxabicyclo[4.4.0]decan-3-one with a diastereoisomeric excess up to 60%. X-Ray diffraction of the 5S stereoisomer, 1H and 13C NMR, and NOE measurements have allowed complete characterization of the two diastereoisomers. These results gave more details about the mechanism of cyclocarbonylation, and particularly the role of the OH group in the substrate. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
