Direct synthesis of tetrahydropyran-4-ones via O3ReOH-catalyzed Prins cyclization of 3-chlorohomoallylic alcohols?

Organic & Biomolecular Chemistry Pub Date: 2022-11-22 DOI: 10.1039/D2OB01941H

Abstract

A new variation of Prins cyclization to directly and stereoselectively synthesize cis-2,6-disubstituted tetrahydropyran-4-ones from 3-chlorohomoallylic alcohols and aldehydes catalyzed by perrhenic acid is reported. The reaction is generally compatible with a range of aliphatic and aromatic aldehydes and 24 examples of tetrahydropyran-4-one products have been prepared in moderate to good yields. This methodology highlights the use of simple starting materials and commercially available aqueous perrhenic acid as a catalyst for Prins cyclization reactions to directly synthesize 2,6-disubstituted tetrahydropyran-4-ones.

Graphical abstract: Direct synthesis of tetrahydropyran-4-ones via O3ReOH-catalyzed Prins cyclization of 3-chlorohomoallylic alcohols
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