Ionic ‘Diels–Alder’ reactions of hexa-3,5-dienyl trimethylsilyl ether and enones: X-ray structural determination of adduct stereostructure, and a stereoselective approach to trans-fused octalin systems

Richard K. Haynes; Kwok-Ping Lam; Ian D. Williams; Lam-Lung Yeung

doi:10.1039/C39950002479

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Journal of the Chemical Society, Chemical Communications

Issue 24, 1995

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Ionic ‘Diels–Alder’ reactions of hexa-3,5-dienyl trimethylsilyl ether and enones: X-ray structural determination of adduct stereostructure, and a stereoselective approach to trans-fused octalin systems

Richard K. Haynes , Kwok-Ping Lam , Ian D. Williams and Lam-Lung Yeung

J. Chem. Soc., Chem. Commun., 1995, 2479-2480

DOI: 10.1039/C39950002479

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Abstract
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The trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) ethers of hexa-3,5-dien-1-ol react with cyclohexenones and an acyclic enone, methyl vinyl ketone (MVK), in the presence of 5–10 mol% of Me₃SiOSO₂CF₃(TMSOTf) in MeCN to provide trans-fused adducts arising via ionic (Gassman-type) Diels–Alder reactions; structural confirmation for adduct stereochemistry for this type of reaction is provided by an X-ray structural determination.

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Journal of the Chemical Society, Chemical Communications

Ionic ‘Diels–Alder’ reactions of hexa-3,5-dienyl trimethylsilyl ether and enones: X-ray structural determination of adduct stereostructure, and a stereoselective approach to trans-fused octalin systems

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