Stereoselective Synthesis of 2,6‐Disubstituted‐4‐Aryltetrahydropyrans Using Sakurai–Hosomi–Prins–Friedel–Crafts Reaction

Abstract

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)

MWW-type zeolite nanostructures for a one-pot three-component Prins–Friedel–Crafts reaction

“…The one-pot multicomponent reaction approach is a powerful and straightforward route to various complex high value-added molecules. 1–4 In particular, multicomponent reactions provide valuable functionalized heterocyclic compounds containing a 4-aryltetrahydropyran moiety, 5–7 which is the core unit of many biologically active compounds including epicalyxin F and calyxins I and L with antiproliferative activity against human fibrosarcoma HT-1080, and murine colon 26-L5 carcinoma cells. 8–11 A one-pot acid-catalyzed Prins–Friedel–Crafts reaction between a carbonyl compound, a homoallylic alcohol and an aromatic hydrocarbon is an efficient method for the synthesis of heterocycles with the 4-aryltetrahydropyran moiety.…”

Synthesis of Heterocyclic Scaffolds via Prins, Oxonium-Ene and Related Cyclization Reactions

“…Similarly, when arene was used instead of nitrile, 4-aryl tetrahydropyran derivatives 15 were obtained in very good yields (Scheme 4). 35 Both aliphatic and aromatic aldehydes were effective in giving excellent yields.…”

Synthesis of O‐ and N‐Heterocycles by Silyl‐Prins Cyclization of Allylsilanes

“…The mechanism involves an initial acid‐catalyzed Sakurai reaction between the allylsilane and the aldehyde to give a homoallylic alkoxide. This intermediate undergoes Prins cyclization in the presence of excess aldehyde to give a secondary tetrahydropyranyl cation, which is finally trapped by the aryl nucleophile (Scheme ) …”