Bismuth-triflate-catalyzed Prins-Ritter reaction - An efficient synthesis of 4-Amidotetrahydropyrans

Yadav, J. S. ; Subba Reddy, B. V. ; Chaya, D. N. ; Narayana Kumar, G. G. K. S. (2008) Bismuth-triflate-catalyzed Prins-Ritter reaction - An efficient synthesis of 4-Amidotetrahydropyrans Canadian Journal of Chemistry, 86 (8). pp. 769-773. ISSN 0008-4042

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Official URL: http://www.nrcresearchpress.com/doi/abs/10.1139/v0...

Related URL: http://dx.doi.org/10.1139/v08-080

Abstract

Bismuth(III) triflate is found to be an effective Lewis acid in catalyzing a three-component reaction of homoallylic alcohol, carbonyl compound, and nitrile at ambient temperature via the Prins-Ritter sequence to furnish 4-amidotetrahydropyrans in high yields, all with cis selectivity. Spirocyclic 4-amidotetrahydropyrans are obtained in case of cyclic ketones.Key words: Prins cyclization, bismuth(III) triflate, homoallyl alcohol, 4-amidotetrahydropyrans.

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Deposited On:28 Sep 2011 03:39
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