Acid-promoted prins cyclizations of enol ethers to form tetrahydropyrans
Acid-promoted prins cyclizations of enol ethers to form tetrahydropyrans
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DOI：
10.1021/ol0342756
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发表时间：
2003-05-01
期刊：
影响因子：
5.2
通讯作者：
Bennett, CE
中科院分区：
文献类型：
--
作者：
Hart, DJ;Bennett, CE
三氟乙酸有效地催化烯醇醚8的Prins环化，得到四氢吡喃9和10。这些四氢吡喃的分离总收率为42-85%，C-4的立体选择性为95：5 - 50：50，取决于取代基R的性质。这些环化反应的独特副产物揭示了潜在平衡的存在，已被分离和鉴定。
[GRAPHICS]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 stereoselectivitles 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.