Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β-Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones

beta-Silyl-gamma-ethylidene-gamma-butyrolactone upon one-pot treatment with aldehydes and ketones in the presence of Lewis acids underwent a tandem Hosomi-Sakurai/Prins cyclization to give polysubstituted tetrahydropyranones stereoselectively. Various aldehydes and ketones can be used in this reaction to produce the corresponding tetrahydropyranones. The optical purity of the starting gamma-butyrolactone was substantially retained in the resulting tetrahydropyranones.

Automated summary

The reaction proceeded via tandem Hosomi-Sakurai/Prins cyclization to produce polysubstituted tetrahydropyranones with high stereoselectivity. It is compatible with various aldehydes and ketones, and the optical purity of the starting material was well-retained in the final products.