Diastereoselective Synthesis of Substituted Tetrahydrothiophenes and -thiopyrans via Thia-Prins Cyclization Reaction

Tetrahydrothiophenes and -thiopyrans have been efficiently synthesized from thioacrylates via thia-Prins cyclization reaction mediated by trimethyl­silyl­trifluoro­methane­sulfonate with good diastereoselectivity and in good to high yields.以三甲基硅基三氟甲磺酸酯（trimethylsilyltrifluoromethanesulfonate）为反应介导试剂，通过硫代Prins环化反应（thia-Prins cyclization reaction），可由硫代丙烯酸酯（thioacrylates）高效合成四氢噻吩（Tetrahydrothiophenes）与四氢噻喃类化合物，该反应具有良好的非对映选择性，产物收率处于良好至较高水平。