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Communication | Special issue | Vol 70, No. 1, 2006, pp.119-128
Published online, 17th October, 2006
DOI: 10.3987/COM-06-S(W)39
Substituent Effects on the Regiochemical and Stereochemical Course of the Nussbaumer-Frater Variation of the Prins Cyclization

Chad E. Bennett, Ruth Figueroa, David J. Hart,* and Dexi Yang

*Department of Chemistry, The Ohio State University, 100 West 18th Avenue Columbus, Ohio 43210, U.S.A.


Eleven vinylogous carbonates were examined in the Nussbaumer-Frater variation of the Prins cyclization to provide 2,3,4,6-tetrasubstituted tetrahydropyrans. Results indicate that substrate olefin geometry is a more reliable control element than preset substrate vicinal stereochemistry for establishing C2-C3 vicinal stereochemistry in tetrahydropyran products.