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100 | 1 | _ | |a Weber, Anja |0 P:(DE-HGF)0 |b 0 |
245 | _ | _ | |a Experimental and Computational Investigations of the Reactions between α,β‐Unsaturated Lactones and 1,3‐Dienes by Cooperative Lewis Acid/Brønsted Acid Catalysis |
260 | _ | _ | |a Weinheim |c 2020 |b Wiley-VCH |
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520 | _ | _ | |a The 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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700 | 1 | _ | |a Breugst, Martin |0 P:(DE-HGF)0 |b 1 |e Corresponding author |
700 | 1 | _ | |a Pietruszka, Jörg |0 P:(DE-Juel1)128906 |b 2 |e Corresponding author |u fzj |
773 | _ | _ | |a 10.1002/anie.202008365 |g Vol. 59, no. 42, p. 18709 - 18716 |0 PERI:(DE-600)2011836-3 |n 42 |p 18709 - 18716 |t Angewandte Chemie / International edition |v 59 |y 2020 |x 1521-3773 |
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