A simple and expeditious synthesis of 2,3,6-trisubstituted tetrahydropyrans through (3,5)-oxonium-ene cyclization using molecular iodine

A variety of aldehydes undergo a smooth coupling with 6-methylhept-5-en-2ol in the presence of molecular iodine to afford the 2,3,6-trisubstituted tetrahydropyrans in good yields through 3,5-oxonium-ene cyclization under mild and neutral conditions. This method is simple, convenient, and cost-effect...

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Bibliographic Details
Published in:Tetrahedron letters 2013-07, Vol.54 (28), p.3639-3642
Main Authors: Prudhvi Raju, N., Jagan Mohan Reddy, B., Anjibabu, R., Muralikrishna, K., Subba Reddy, B.V.
Format: Article
Language:English
Subjects:
3-Isopropenyl-6-methyltetrahydropyrans
Aldehydes
Alkenols
Coupling (molecular)
Iodine
Molecular iodine
Oxonium-ene reaction
Synthesis (chemistry)
Tetrahedrons
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Summary:A variety of aldehydes undergo a smooth coupling with 6-methylhept-5-en-2ol in the presence of molecular iodine to afford the 2,3,6-trisubstituted tetrahydropyrans in good yields through 3,5-oxonium-ene cyclization under mild and neutral conditions. This method is simple, convenient, and cost-effective.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.04.104