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 |
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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 |