Diastereoselective Prins-Type Reaction of Cycloalkenylcyclopropanol Silyl Ethers and α,β-Unsaturated Aldehyde Acetals

Gallium tribromide catalyzed coupling reaction of alkenyl ethers with ketene silyl acetals.

Silyl Enol Ether Prins Cyclization: Diastereoselective Formation of Substituted Tetrahydropyran-4-ones

A diastereoselective synthesis of cis-2,6-disubstituted tetrahydropyran-4-ones was developed. The key step of this methodology, a silyl enol ether Prins cyclization, was promoted by a condensation reaction between a hydroxy silyl enol ether and an aldehyde to afford substituted tetrahydropyran-4-ones. The cyclization was tolerant of many functional groups, and the modular synthesis of the hydro...

A versatile indium trichloride mediated Prins-type reaction to unsaturated heterocycles.

A versatile and high-yielding indium trichloride mediated cyclization reaction of silylated homoallylic alcohols, thiols, or amines with aldehydes or epoxides is described as a rapid route to a range of unsaturated heterocycles. The excellent diastereoselectivity observed offers a method of wide scope and generality.

Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones.

The unified Ir-catalyzed enantioselective allylic substitution reactions of silyl enol ethers derived from ketones and α,β-unsaturated ketones with branched, racemic allylic alcohols are described. This transformation is catalyzed by the Carreira system and proceeds without fluoride, and with high ee and b : l ratio. The synthetic utility of this method was illustrated by the concise enantiosel...

Iodotrimethylsilane-mediated additions of dienol silyl ethers to .alpha.,.beta.-unsaturated ketones

Trimethylsily1)oxy-substituted dienes react with 1 at low temperatures to afford annulated products. Disciplines Chemistry | Environmental Chemistry | Inorganic Chemistry | Organic Chemistry | Other Chemistry | Polymer Chemistry Comments Reprinted (adapted) with permission from The Journal of Organic Chemistry, 49(6); 1153-1154. Doi: 10.1021/jo00180a048. Copyright 1984 American Chemical Society...