Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction
| Autor: | Alicia McGhee, Forrest E. Michael, Brian M. Cochran, Torrey A. Stenmark |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Chemistry
Morpholines Metals and Alloys Diastereomer chemistry.chemical_element Stereoisomerism General Chemistry Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials Nucleophile Materials Chemistry Ceramics and Composites Organic chemistry Stereoselectivity Lewis acids and bases Hydroamination Palladium Amination |
| Zdroj: | Chemical Communications. 49:6800 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c3cc44117b |
| Popis: | A palladium-catalyzed hydroamination reaction is the key step in a stereoselective synthesis of 2,5-disubstituted and 2,3,5-trisubsituted morpholines from carbamate-protected aziridines. Aziridines are selectively attacked at the more substituted position by unsaturated alcohol nucleophiles using Lewis acid catalysts. Palladium-catalyzed hydroamination of the resulting aminoalkenes gives morpholines as a single diastereomer in excellent yield. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|