Acid-promoted Prins cyclizations of enol ethers to form tetrahydropyrans |
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| Authors: | Hart David J Bennett Chad E |
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| Affiliation: | Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA. hart@chemistry.ohio-state.edu |
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| 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] |
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