Diels−Alder reactions of a range of
(R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones
with cyclopentadiene and 1,3-pentadiene proceed in a total π-facial
diastereoselective 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.
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