Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 12, Pages 3707-3719Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902796
Keywords
boron; Diels-Alder reactions; quinones; regioselectivity; fused adducts
Categories
Funding
- MICINN [CTQ2008-04961]
- Comunidad de Madrid (CM)/UAM [CCG08-UAM/PPQ-3980, SOLGEMAC-S2009/ENE-1617]
- CM [S2009/ENE-1617]
- MEC
- M V
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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.
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