Three-component synthesis of 2-aryl-4-arylthio-tetrahydro-2H-pyrans via the Prins-cyclization

A three-component coupling of aldehyde, homoallylic alcohol and aryl thiol, has been achieved in the presence of trifluoroacetic acid in dichloromethane at room temperature to produce 4-arylthiotetrahydropyrans in good yields with all cis-selectivity. This method is simple, selective and convenient for introducing a thiol group on a tetrahydropyran ring. (C) 2009 Elsevier Ltd. All rights reserved.