Synthesis of 3-Aryl-Substituted Tetrahydropyran-4-ones and Tetrahydrothiopyran-4-ones

A series of tetrahydropyran-4-one and tetrahydrothio­pyran-4-one derivatives with 3-aryl or 3,6-diaryl substituents were prepared by double conjugate addition of water or H2S to divinyl ketones. These starting materials were accessed in two steps by ­conversion of lithiated (alpha)-bromostyrene derivatives with acrolein or cinnamaldehyde and subsequent oxidation of the divinylalcohols with MnO2.