Weber, Anja, Breugst, Martin 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

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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:
CreatorsEmailORCIDORCID Put Code
Weber, AnjaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Breugst, MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Pietruszka, JoergUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
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: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
DIELS-ALDER REACTION; STRUCTURE ELUCIDATION; ONE-POT; PSYMBERIN; PEDERIN; CLADOSPORIN; DERIVATIVES; KETONES; FUNGIMultiple languages
Chemistry, MultidisciplinaryMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/32308

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