Premium Experimental and Computational Investigations of the Reactions between α,β‐Unsaturated Lactones and 1,3‐Dienes by Cooperative Lewis Acid/Brønsted Acid CatalysisPremium
angewandte chemie international edition
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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