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.

No abstract

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.

The reaction of aldehydes with allyltrimethylsilane in arene solvents gives symmetrical 2,6‐disubstituted‐4‐aryltetrahydropyrans in good yields. The reaction is highly stereoselective. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)