208447-85-2Relevant academic research and scientific papers
Studies of Diastereoselectivity in Conjugate Addition of Organoaluminum Reagents to (R)-[(p-Tolylsulfinyl)methyl]quinols and Derivatives
Carreno, M. Carmen,González, Manuel Pérez,Ribagorda, María,Houk
, p. 3687 - 3693 (1998)
(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-alkylsubstituted analogues 4 and 5 and 5-alkyl-4-hydroxy-4-[(p-tolylsuIfinyl)methyl]-2-cyclohexenones 10a,b. Semiempirical calculations (AM1 model) provide data on transition-state energies for additions in full agreement with the experimental results.
