HETEROCYCLES

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

■ 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.

Abstract

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.