Faculté des sciences
Texte intégral

Diastereoselective synthesis of (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride

Marty, Maurus ; Stoeckli-Evans, Helen ; Neier, Reinhard

In: Tetrahedron, 1996, vol. 52, no. 13, p. 4645-4658

While attempting to synthesize a potential inhibitor of the biosynthetic step of formation of PBG, a novel catalytic system inducing the Prins reaction was discovered. Treatment of epoxy geranial with Zn and trimethylsilyl chloride gave (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol in high diastereoselectivity. More

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    Title
    • Diastereoselective synthesis of (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride
    Author
    • Marty, Maurus. Institut de Chimie, Université de Neuchâtel, Switzerland
    • Stoeckli-Evans, Helen. Institut de Chimie, Université de Neuchâtel, Switzerland
    • Neier, Reinhard. Institut de Chimie, Université de Neuchâtel, Switzerland
    Document Type
    • Postprint
    Publication Date
    • 1996
    Classification
    • Chemistry
    OAI-PMH Identifier
    • oai:doc.rero.ch:20070827162437-VA
    Submission No.
    • 20070827162437-VA
    Summary
    While attempting to synthesize a potential inhibitor of the biosynthetic step of formation of PBG, a novel catalytic system inducing the Prins reaction was discovered. Treatment of epoxy geranial with Zn and trimethylsilyl chloride gave (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol in high diastereoselectivity.