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

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-cyclohexanedi...

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Bibliographic Details
Published in:Tetrahedron 1996-03, Vol.52 (13), p.4645-4658
Main Authors: Marty, Maurus, Stoeckli-Evans, Helen, Neier, Reinhard
Format: Article
Language:English
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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. Zn and TMS-Cl a novel catalytic system induces the Prins reaction of epoxigeranial with high diastereoselectivity.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00167-6