An Enamide-BasedDomino Reactionfor aHighlyStereoselectiveSynthesisof Tetrahydropyrans
- A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ-bonds and five continuous stereogenic centers are formed in this one-pot process with a remarkable degree of diastereoselectivity. In most cases, the formation of only one out of 16 possible diastereomers is observed. Two different stereoisomers can be accessed in a controlled fashion starting either from an E- or a Z-configured enamide.
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| Author: | Philipp KramerORCiD, Jennifer Grimmer, Michael BolteORCiD, Georg ManolikakesORCiD |
|---|---|
| URN: | urn:nbn:de:hbz:386-kluedo-79646 |
| DOI: | https://doi.org/10.1002/anie.201907565 |
| ISSN: | 1521-3773 |
| Parent Title (English): | Angewandte Chemie International Edition |
| Publisher: | Wiley |
| Document Type: | Article |
| Language of publication: | English |
| Date of Publication (online): | 2024/04/08 |
| Year of first Publication: | 2019 |
| Publishing Institution: | Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau |
| Date of the Publication (Server): | 2024/04/08 |
| Issue: | 58/37 |
| Page Number: | 4 |
| First Page: | 13056 |
| Last Page: | 13059 |
| Source: | https://onlinelibrary.wiley.com/doi/10.1002/anie.201907565 |
| Faculties / Organisational entities: | Kaiserslautern - Fachbereich Chemie |
| DDC-Cassification: | 5 Naturwissenschaften und Mathematik / 540 Chemie |
| Collections: | Open-Access-Publikationsfonds |
| Licence (German): | Lizenz nach Originalpublikation |