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Paper | Special issue | Vol 74, No. 1, 2007, pp.447-459
Published online, 21st September, 2007
DOI: 10.3987/COM-07-S(W)23
Electrophile-Induced Ether Transfer: An Expedient Route to 2-Cyanotetrahydropyrans

Rendy Kartika and Richard E. Taylor*

*Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556, U.S.A.

Abstract

Electrophile-induced ether transfer reactions of alkoxymethyl ether protected homoallylic alcohols with cyanide quench provide cyanoether adducts in high yield and excellent 1,3-syn-stereoselectivity. Subsequent base-mediated cyclization then provides the corresponding 2,4,6-trisubstituted cyano-tetrahydropyran.