Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols.

@article{Carreo2007EnantioselectiveSO,
  title={Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols.},
  author={M. Carmen Carre{\~n}o and Est{\'i}baliz Merino and Mar{\'i}a Ribagorda and {\'A}lvaro Somoza and Antonio Urbano},
  journal={Chemistry},
  year={2007},
  volume={13 4},
  pages={
          1064-77
        }
}
Exploitation of the beta-hydroxysulfoxide fragment present in a number of enantiomerically pure (SR)- and (SS)-[(p-tolylsulfinyl)methyl]-p-quinols allowed chemo- and stereocontrolled conjugate additions of different organoaluminium reagents to the cyclohexadienone moiety. The same fragment was also shown to act as an efficient chiral masking carbonyl group, after oxidation to sulfone and retroaddition in basic medium, with elimination of methyl p-tolyl sulfone. Through the use of both… 
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