Benzyl chlorides as aldehyde surrogates in the Prins cyclization: Direct access to 2-aryl-4-chlorotetrahydropyrans

Abstract

An efficient synthesis of 2-aryl-4-chloro-tetrahydropyrans has been accomplished from benzyl chlorides and homoallylic alcohols using FeCl3 as a promoter through a sequential oxidation/Prins cyclization in high yields. This is the first report on the use of benzyl chlorides as surrogates for aldehydes in the Prins cyclization.