Stereoselective synthesis of substituted tetrahydrofurans using 5- endo-trig cyclisation reactions

Sulfonyl-substituted homoallylic alcohols undergo 5- endo-trig cyclisation reactions on treatment with base, with cyclisation stereoselectivity depending on double bond geometry. Sulfonyl-substituted homoallylic alcohols 3 undergo stereoselective 5- endo-trig cyclisation reactions to give tetrahydro...

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Bibliographic Details
Published inTetrahedron Vol. 55; no. 47; pp. 13471 - 13494
Main Authors Craig, Donald, Ikin, Neil J., Mathews, Neil, Smith, Alison M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.11.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
cyclisation
Physical Sciences
Science & Technology
sulfone
synthesis
tetrahydrofuran
synthesis
cyclisation
tetrahydrofuran
sulfone
CYCLIZATIONS
ROUTES
SULFONES
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Summary:Sulfonyl-substituted homoallylic alcohols undergo 5- endo-trig cyclisation reactions on treatment with base, with cyclisation stereoselectivity depending on double bond geometry. Sulfonyl-substituted homoallylic alcohols 3 undergo stereoselective 5- endo-trig cyclisation reactions to give tetrahydrofurans 8 Some derivatisation reactions of the product syn- 8a (R 1 = R 2 = Me) are reported.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00832-7