In(OTf) 3-catalyzed synthesis of 4-thiocyanotetrahydropyrans via a three-component reaction

A three-component coupling of aldehydes, homoallylic alcohols and ammonium thiocyanate is achieved in the presence of 10 mol % of In(OTf) 3 in refluxing dichloromethane to produce 4-thiocyanotetrahydropyrans in excellent yields with all cis-selectivity. This method is simple, selective and convenien...

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Bibliographic Details
Published in:Tetrahedron letters 2007-12, Vol.48 (50), p.8874-8877
Main Authors: Yadav, J.S., Subba Reddy, B.V., Maity, Tapas, Narayana Kumar, G.G.K.S.
Format: Article
Language:English
Subjects:
4-Thiocyanotetrahydropyrans
Prins-cyclization
Three-component reaction
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Summary:A three-component coupling of aldehydes, homoallylic alcohols and ammonium thiocyanate is achieved in the presence of 10 mol % of In(OTf) 3 in refluxing dichloromethane to produce 4-thiocyanotetrahydropyrans in excellent yields with all cis-selectivity. This method is simple, selective and convenient for introducing an SCN group onto a tetrahydropyran ring.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.10.047