Premium Experimental and Computational Investigations of the Reactions between α,β‐Unsaturated Lactones and 1,3‐Dienes by Cooperative Lewis Acid/Brønsted Acid Catalysis
Weber Anja,
Breugst Martin,
Pietruszka Jörg
Publication year2020
Publication title
angewandte chemie international edition
Resource typeJournals
Abstract 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.
Subject(s)brønsted–lowry acid–base theory , catalysis , chemistry , diene , epistemology , isocoumarin , kinetics , lewis acid catalysis , lewis acids and bases , mechanism (biology) , medicinal chemistry , natural rubber , order of reaction , organic chemistry , philosophy , physics , quantum mechanics , reaction mechanism , reaction rate constant , stepwise reaction , trimethylsilyl
Keyword(s) catalysis , computational chemistry , density functional calculations , Michael additions , natural products
SCImago Journal Rank5.831

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