Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)3/LiI system as the promoter

The rapid and regioselective synthesis of a series of 2,6-disubstituted dihydropyranic building-blocks bearing an oxygenated side chain is described. The corresponding 4-iodo tetrahydropyran precursors, easily prepared by Prins cyclization, underwent regioselective elimination in the presence of an...

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Bibliographic Details
Published inTetrahedron Vol. 72; no. 2; pp. 318 - 327
Main Authors Chalopin, Thibaut, Jebali, Khaoula, Gaulon-Nourry, Catherine, Dénès, Fabrice, Lebreton, Jacques, Mathé-Allainmat, Monique
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 14.01.2016
Subjects
Elimination
Lewis acid
Oxygen heterocycles
Prins cyclization
Regioselectivity
Lewis acid
Oxygen heterocycles
Regioselectivity
Elimination
Prins cyclization
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Summary:The rapid and regioselective synthesis of a series of 2,6-disubstituted dihydropyranic building-blocks bearing an oxygenated side chain is described. The corresponding 4-iodo tetrahydropyran precursors, easily prepared by Prins cyclization, underwent regioselective elimination in the presence of an In(OAc)3/LiI system to provide the title compounds. The one-pot Prins cyclization-elimination process was also studied and could be achieved with the TMSBr/LiI/In(OAc)3 system. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.11.046