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- W2096005886 endingPage "3719" @default.
- W2096005886 startingPage "3707" @default.
- W2096005886 abstract "Abstract Substituted 2‐quinonyl boronic acids have been synthesised from 1,4‐dimethoxy aromatic derivatives in two steps: regiocontrolled boronation and oxidative demethylation. The study of their dienophilic behaviour evidenced that the boron substituent significantly increases the reactivity and triggers an efficient domino process in which the Diels–Alder reaction was followed by a protodeboronation or dehydroboronation, depending on the substitution on both the quinone and diene partners. The boronic acid acts as a temporary controller, opening a direct access to trans‐ fused meta ‐regiosomeric adducts when 3‐methyl‐substituted 2‐quinonyl boronic acids react with dienes with a substituent at C‐1. A particularly valuable synthetic result was obtained in the reaction between 3,6‐dimethyl‐2‐quinonyl boronic acid and piperylene under an oxygen atmosphere; trans ‐fused 8a‐hydroxy‐2,4a,8‐trimethyl tetrahydronaphthoquinone was formed directly, in excellent yield and in a highly diastereoselective manner." @default.
- W2096005886 created "2016-06-24" @default.
- W2096005886 creator A5011514503 @default.
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- W2096005886 creator A5060745914 @default.
- W2096005886 creator A5064075040 @default.
- W2096005886 creator A5083302387 @default.
- W2096005886 date "2010-03-16" @default.
- W2096005886 modified "2023-10-18" @default.
- W2096005886 title "Synthesis of Benzo- and Naphthoquinonyl Boronic Acids: Exploring the Diels-Alder Reactivity" @default.
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