A diastereoselective one-pot, three-component Prins-Friedel-Crafts reaction was developed for the synthesis of 4-aryltetrahydropyran derivatives from the reaction of carbonyl compounds with homoallylic alcohol in the presence of arene promoted by boron trifluoride etherate.
The reaction of aldehyde with allylsilane in acetonitrile mediated by boron trifluoride etherate generated 4-aminotetrahydropyrans in good yields. The product is highly stereoselective.
Oxabicyclo[3.3.1]nonanone can conveniently be prepared by the reaction of trans-p-menth-6-ene-2,8-diol and aldehyde or epoxide mediated by boron trifluoride etherate in good yields. The reaction proceeds via (3,5)-oxonium-ene-type reaction.
An efficient method has been developed for the synthesis of 2,3-dihydropyrans and 4-methylenetetrahydropyrans from aldehydes and substituted homoallyl alcohols in benzene mediated by boron trifluoride etherate in good yields. The reaction proceeds via oxonium-ene reaction.
An efficient method for the synthesis of 4-aryldihydropyrans has been developed from the reaction of aldehydes or epoxides with homopropargylic alcohols in the presence of arenes promoted by boron trifluoride etherate
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