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Et 3 Al/Light-Promoted Radical-Polar Crossover Reactions of α-Alkoxyacyl Tellurides.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2024 Aug 16; Vol. 89 (16), pp. 11701-11706. Date of Electronic Publication: 2024 Aug 07. - Publication Year :
- 2024
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Abstract
- Here, we report new radical-polar crossover reactions of α-alkoxy carbon radicals for constructing highly oxygenated molecules with contiguous stereocenters. The method employs a 370 nm UV light-emitting diode (LED) for the photoexcitation of α-alkoxyacyl telluride, and Et <subscript>3</subscript> Al as the radical initiator and terminator. First, Et <subscript>3</subscript> Al and UV LED promoted radical coupling between the α-alkoxyacyl telluride and cyclopentenone via C-Te bond homolysis, CO expulsion, and C-C bond formation. Second, Et <subscript>3</subscript> Al converted the radical species to the corresponding aluminum enolate. Third, the second C-C bond formation occurred via a polar mechanism: intermolecularly with aldehydes/ketones and intramolecularly with epoxide, producing aldol and S <subscript>N</subscript> 2 adducts, respectively. The present coupling reactions increase the molecular complexity in a single step by stereoselective formation of the two hindered C-C bonds. The devised method is expected to be useful for the expeditious assembly of densely oxygenated natural products.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 89
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39110480
- Full Text :
- https://doi.org/10.1021/acs.joc.4c01445