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 |
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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 |