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  • 1
    ISSN: 1434-193X
    Keywords: Asymmetric dihydroxylation (Sharpless-AD) ; Wittig olefination ; α-Bromo α,β-unsaturated esters ; Diastereoselective aprotic Michael domino reaction ; Tricyclo[3.2.1.02,7]octanes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The chiral α-bromo α,β-unsaturated esters 3 and 9 are prepared by asymmetric Sharpless dihydroxylation (AD) of 5 and from ester 7 and the chiral diols 8 by transacetalization, respectively. Both types of α-bromo α,β-unsaturated ester react with the kinetic lithium dienolates of enone 10 to give functionalized tricyclo[3.2.1.02,7]octanes 11. Esters 3 give one single diastereomer (de ≥ 95%), whereas mixtures of diastereomers (de 28 to 46%) are obtained with the esters 9.
    Type of Medium: Electronic Resource
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