Stereoselective synthesis of dienyl phosphonates via extended tethered ring-closing metathesis
- Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.
| Author details: | Bernd SchmidtORCiDGND, Oliver Kunz |
|---|---|
| DOI: | https://doi.org/10.1021/ol4020078 |
| ISSN: | 1523-7060 |
| ISSN: | 1523-7052 |
| Title of parent work (English): | Organic letters |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2013 |
| Publication year: | 2013 |
| Release date: | 2017/03/26 |
| Volume: | 15 |
| Issue: | 17 |
| Number of pages: | 4 |
| First page: | 4470 |
| Last Page: | 4473 |
| Funding institution: | Deutsche Forschungsgemeinschaft (DFG) [Schm 1095/6-3] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
