Pagire, Santosh K. and Hossain, Asik and Traub, Lukas and Kerres, Sabine and Reiser, Oliver (2017) Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes. CHEMICAL COMMUNICATIONS, 53 (89). pp. 12072-12075. ISSN 1359-7345, 1364-548X
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An efficient method for the synthesis of substituted cyclobutanes from cinnamates, chalcones, and styrenes has been developed utilizing a visible-light triplet sensitisation mode. This reaction provides a diverse range of substituted cyclobutanes in high yields under mild conditions without the need of external additives. Good regioselectivity is obtained due to strong p-p-stacking of arene moieties, whereas diastereoselectivity relies on the electronic effects or ortho-substitution of the arene substrate. The utility of this transformation is demonstrated by the formal synthesis of the lignane natural product (+/-)-Tanegool.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | VISIBLE-LIGHT PHOTOCATALYSIS; INTERMOLECULAR 2+2 CYCLOADDITION; CLEAVABLE REDOX AUXILIARIES; TRANSFER RADICAL-ADDITION; PHOTOREDOX CATALYSIS; ORGANIC-SYNTHESIS; ENERGY-TRANSFER; CYCLOBUTANE DERIVATIVES; ALPHA-BROMOCHALCONES; STRUCTURAL REVISION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:19 |
| Last Modified: | 26 Feb 2019 10:27 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1834 |
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