Stereoselective, One-Pot, Three-Component Synthesis of 4-Aryltetrahydropyrans from Epoxides via Prins Cyclization Reaction (original) (raw)

The reaction of aldehyde with allylsilane in acetonitrile mediated by boron trifluoride etherate generated 4-aminotetrahydropyrans in good yields. The product is highly stereoselective. Multicomponent reactions are gaining interest in organic synthesis due to its ability to form multiple bonds in a single step. 1 Substituted tetrahydropyrans are important targets because of their presence in many natural products. 2 These tetrahydropyrans are prepared by hetero-Diels-Alder methods, 3 manipulation of carbohydrates, 4 Prins cyclization, 5 and intramolecular Michael reactions. 6 Although there are a few methods for the synthesis of 4-halo-, 7 4-thio-, 8 4-azido-, 9 4-aryl-, 10 and 4-hydroxytetrahydropyran, 5e,f,7d,11 methods for the synthesis of 4-aminotetrahydropyran are limited. 12 In this paper, an efficient method for the synthesis of 4 aminotetrahydropyran from aldehyde, trimethylallylsilane, and acetonitrile mediated by BF 3 ‚ Et 2 O is disclosed (Scheme 1). Thus, when benzaldehyde was subjected to react with allyltrimethylsilane in acetonitrile in the presence of boron trifluoride etherate, 4-acetamido-2,6-diphenyltetrahydrofuran was obtained in 70% yield.

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