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Acid-promoted Prins cyclizations of enol ethers to form tetrahydropyrans
1Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA. hart@chemistry.ohio-state.edu
Organic Letters
|April 26, 2003
Abstract:
Trifluoroacetic acid efficiently catalyzes Prins cyclizations of enol ethers 8 to provide tetrahydropyrans 9 and 10. These tetrahydropyrans are isolated with combined yields of 42-85% and stereoselectivities at C(4) ranging from 95:5 to 50:50 depending on the nature of the substituent R. Unique byproducts of these cyclizations that reveal the presence of underlying equilibria have been isolated and identified. [reaction: see text]