ChemInform Abstract: m-CPBA-Mediated Stereoselective Synthesis of Sulfonyl Tetrahydropyrans

A stereoselective synthesis of sulfonyl tetrahydropyrans (THPs) 6 was performed with moderate to good yields by m-CPBA (m-chloroperoxybenzoic acid)-mediated ring-closure of β-hydroxy sulfones 5. Skeleton 5 is prepared by cinnamylation of β-ketosulfones 3 in the presence of K2CO3 followed by NaBH4-mediated reduction of the resulting skeleton 4 with a α-cinnamyl side arm in the co-solvent of THF and MeOH. The key structures of skeleton 6 were confirmed by X-ray crystallographic analysis. The reaction mechanism had been discussed.