Competitive intramolecular Diels-Alder reactions of bis-a,ß-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols. Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes

Martin Banwell, Chonhoon Chun, Alison Edwards, Markus Vogtle

    Research output: Contribution to journalArticle

    Abstract

    bis-Crotonate and related alpha;,?-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels-Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.
    Original languageEnglish
    Pages (from-to)861-869
    JournalAustralian Journal of Chemistry
    Volume56
    Issue number9
    DOIs
    Publication statusPublished - 2003

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