Auxiliary controlled singlet-oxygen ene reactions of cyclohexenes
- The photooxygenation of homochiral cyclohexene ketals, which are easily available from 2-cyclohexenone and L-tartrates, affords hydroperoxides and after reduction the corresponding allylic alcohols in good yields and high regioselectivities. This can be rationalized by electronic repulsions in a perepoxide intermediate and provides evidence for unfavorable 1,3 diaxial interactions with a dioxolane oxygen atom. Only low stereoselectivities were observed, due to the flexibility of the cyclohexene ring. However, the diastereomers could be separated and after cleavage of the auxiliary, 4-hydroxy-2-cyclohexen-1-one was isolated in enantiomerically pure form, which can serve as a building block for natural product synthesis.
| Author details: | Werner FudickarORCiDGND, Katja Vomdran, Torsten LinkerORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1016/j.tet.2006.07.104 |
| ISSN: | 0040-4020 |
| Title of parent work (English): | Tetrahedron |
| Publisher: | Elsevier |
| Place of publishing: | Oxford |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2006/11/13 |
| Publication year: | 2006 |
| Release date: | 2020/05/03 |
| Tag: | auxiliary control; regioselectivity; singlet oxygen; stereoselectivity |
| Volume: | 62 |
| Issue: | 46 |
| Number of pages: | 8 |
| First page: | 10639 |
| Last Page: | 10646 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
