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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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| Published in: | Tetrahedron 2012-03, Vol.68 (10), p.2261-2266 |
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| Main Authors: | , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c360t-d5c70b9a7bc724bdd199823e6241531b28b813aa2e48e7e19e36d0f9fc632b223 |
| container_end_page | 2266 |
| container_issue | 10 |
| container_start_page | 2261 |
| container_title | Tetrahedron |
| container_volume | 68 |
| creator | Saha, Pipas Saikia, Anil K. |
| description | 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.
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| doi_str_mv | 10.1016/j.tet.2012.01.064 |
| format | article |
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| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
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| language | eng |
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| source | Elsevier |
| 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 |
| title | Stereoselective synthesis of 6-oxabicyclo[3.2.1]octene via (3,5)-oxonium-ene reaction |
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