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  • 1
    ISSN: 1434-193X
    Keywords: Cascade reaction ; Aprotic Michael reaction ; Tricyclo[,7]octanes ; Bicyclo[3.2.1]octanes ; Deprotonated cyclopropanes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2′-Alkoxytricyclo[,7]octanes 4-R are obtained in good to excellent yields from methyl 2-chloro-2-cyclopropylideneacetate (3) and the dienolates derived from the 3-alkoxycyclohex-2-enones 1-R and 2-R, by a cascade of two consecutive Michael additions and a γ-elimination. Compounds 4-R are transformed to the correspondingly substituted bicyclo[3.2.1]octanecarboxylates 5 by treatment with acid. 2′-Methoxytricyclooctanes 4a-d-Me are readily deprotonated to give chelation-stabilized cyclopropyllithium derivatives 6-Me, which react with electrophiles to yield the 7′-substituted tricyclo[,7]octanes 4f-i-Me (61-66%). By acidic workup of such reaction mixtures, or subsequent treatment of the isolated products 4f-i-Me with acid, efficient transformation to the correspondingly substituted bicyclo[3.2.1]octanecarboxylates 5 is observed.
    Type of Medium: Electronic Resource
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