π-facial diastereoselection in diels-alder reactions of (R)-4-[(p-tolylsulfinyl)methyl]quinols

摘要

Diels-Alder reactions of a rqange of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]methyl]-2,5-cyclohexadienones with cyclopentadinene and 1,3-pentadiene proceed in a total π-facial diasteroselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G* theory level provide data on transition- state energies for cycloadditions with cyclopentadiene in full agreement with the experimental results.