Olefin-Metathesis-Based Synthesis of Furans by an RCM/Deprotonation/Phosphorylation Sequence and Their Diels-Alder Reactions
- Butenolides, obtained by ring-closing metathesis (RCM) of acrylates, undergo quantitative deprotonation with amide bases. Trapping of the resulting anions with electrophiles, for example, chlorophosphates, give furans. Subsequent DielsAlder reaction and acid-catalysed rearrangement of the resulting oxabicyclonorbornadienes give substituted benzenes.
| Author details: | Bernd SchmidtORCiDGND, Diana Geissler |
|---|---|
| DOI: | https://doi.org/10.1002/ejoc.201101078 |
| ISSN: | 1434-193X |
| Title of parent work (English): | European journal of organic chemistry |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2011 |
| Publication year: | 2011 |
| Release date: | 2017/03/26 |
| Tag: | Lactones; Metalation; Metathesis; Oxygen heterocycles; Ruthenium |
| Issue: | 35 |
| Number of pages: | 8 |
| First page: | 7140 |
| Last Page: | 7147 |
| Funding institution: | Deutsche Forschungsgemeinschaft |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
