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000885456 1001_ $$0P:(DE-HGF)0$$aWeber, Anja$$b0
000885456 245__ $$aExperimental and Computational Investigations of the Reactions between α,β‐Unsaturated Lactones and 1,3‐Dienes by Cooperative Lewis Acid/Brønsted Acid Catalysis
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000885456 520__ $$aThe reactions of α,β‐unsaturated δ‐lactones with activated dienes such as 1,3‐dimethoxy‐1‐[(trimethylsilyl)oxy]‐1,3‐butadiene (Brassard's diene) are barely known in literature and show high potential for the synthesis of isocoumarin moieties. An in‐depth investigation of this reaction proved a stepwise mechanism via the vinylogous Michael‐products. Subsequent cyclisation and oxidation by LHMDS and DDQ, respectively, provided six mellein derivatives (30–84 %) and four angelicoin derivatives (40–78 %) over three steps. DFT‐calculations provide insights into the reaction mechanism and support the theory of a stepwise reaction.
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000885456 7001_ $$0P:(DE-HGF)0$$aBreugst, Martin$$b1$$eCorresponding author
000885456 7001_ $$0P:(DE-Juel1)128906$$aPietruszka, Jörg$$b2$$eCorresponding author$$ufzj
000885456 773__ $$0PERI:(DE-600)2011836-3$$a10.1002/anie.202008365$$gVol. 59, no. 42, p. 18709 - 18716$$n42$$p18709 - 18716$$tAngewandte Chemie / International edition$$v59$$x1521-3773$$y2020
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