Stereoselective synthesis of 6-oxabicyclo[3.2.1]octene via (3,5)-oxonium-ene reaction

Oxabicyclo[3.2.1]octene can efficiently be synthesized by the reaction of (−)-terpinen-4-ol and aldehyde or epoxide catalyzed by indium triflate (In(OTf)3) in good yields. The reaction is stereoselective and proceeds via (3,5)-oxonium-ene-type reaction. [Display omitted]

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Bibliographic Details
Published in:Tetrahedron 2012-03, Vol.68 (10), p.2261-2266
Main Authors: Saha, Pipas, Saikia, Anil K.
Format: Article
Language:English
Subjects:
Aldehydes
Alicyclic compounds, terpenoids, prostaglandins, steroids
Catalytic reaction
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Indium
Indium (III) triflate
Organic chemistry
Oxabicyclic compound
Oxonium-ene reaction
Preparations and properties
Stereoselective
Synthesis (chemistry)
Terpenoids
Tetrahedrons
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Description
Summary:Oxabicyclo[3.2.1]octene can efficiently be synthesized by the reaction of (−)-terpinen-4-ol and aldehyde or epoxide catalyzed by indium triflate (In(OTf)3) in good yields. The reaction is stereoselective and proceeds via (3,5)-oxonium-ene-type reaction. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.01.064