(R)-4-Hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones
1−3, and 6 reacted with
organoaluminum derivatives from the pro-R conjugated position in a
highly π-facial diastereoselective manner
directed by the C-4 OH. A similar facial diastereoselectivity
arose from reactions with 3-alkyl-substituted analogues 4 and 5 and
5-alkyl-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2-cyclohexenones
10a,b. Semiempirical calculations (AM1 model) provide
data on transition-state energies for
additions in full agreement with the experimental results.
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