Weber, Anja, Breugst, Martin ORCID: 0000-0003-0950-8858 and Pietruszka, Joerg (2020). Experimental and Computational Investigations of the Reactions between alpha,beta-Unsaturated Lactones and 1,3-Dienes by Cooperative Lewis Acid/Bronsted Acid Catalysis. Angew. Chem.-Int. Edit., 59 (42). S. 18709 - 18717. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773
Full text not available from this repository.Abstract
The reactions of alpha,beta-unsaturated delta-lactones with activated dienes such as 1,3-dimethoxy-1-[(trimethylsilyl)oxy]-1,3-butadiene (Brassard's diene) are barely known in literature and show high potential for the synthesis of isocoumarin moieties. An in-depth investigation of this reaction proved a stepwise mechanism via the vinylogous Michael-products. Subsequent cyclisation and oxidation by LHMDS and DDQ, respectively, provided six mellein derivatives (30-84 %) and four angelicoin derivatives (40-78 %) over three steps. DFT-calculations provide insights into the reaction mechanism and support the theory of a stepwise reaction.
Item Type: | Journal Article | ||||||||||||||||
Creators: |
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URN: | urn:nbn:de:hbz:38-323084 | ||||||||||||||||
DOI: | 10.1002/anie.202008365 | ||||||||||||||||
Journal or Publication Title: | Angew. Chem.-Int. Edit. | ||||||||||||||||
Volume: | 59 | ||||||||||||||||
Number: | 42 | ||||||||||||||||
Page Range: | S. 18709 - 18717 | ||||||||||||||||
Date: | 2020 | ||||||||||||||||
Publisher: | WILEY-V C H VERLAG GMBH | ||||||||||||||||
Place of Publication: | WEINHEIM | ||||||||||||||||
ISSN: | 1521-3773 | ||||||||||||||||
Language: | English | ||||||||||||||||
Faculty: | Faculty of Mathematics and Natural Sciences | ||||||||||||||||
Divisions: | Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry | ||||||||||||||||
Subjects: | no entry | ||||||||||||||||
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Refereed: | Yes | ||||||||||||||||
URI: | http://kups.ub.uni-koeln.de/id/eprint/32308 |
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