Diastereoselective dearomatization of resorcinols directed by a lactic acid tether: unprecedented enantioselective access to p-quinols.
An operationally simple oxidative dearomatization of resorcinol derivatives is reported that employs an inexpensive chiral directing group. The method provides access to a variety of p-quinol derivatives in good yield and diastereoselectivity. A short reductive process affords 4-hydroxy-4-alkylcyclohexenone derivatives in excellent yields and enantiomeric excesses.
Mejorado
Lupe H
LH
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9150, USA.
Hoarau
Christophe
C
Pettus
Thomas R R
TR
D006873:Hydroquinones / Q000737:chemistry*; D019344:Lactic Acid / Q000737:chemistry*; D015394:Molecular Structure; D012118:Resorcinols / Q000737:chemistry*; D013237:Stereoisomerism
D006873:Hydroquinones; D012118:Resorcinols; D019344:Lactic Acid