title: Diastereoselective dearomatization of resorcinols directed by a lactic acid tether: unprecedented enantioselective access to p-quinols.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9150, USA.
authors.forename: Lupe H
authors.initials: LH
authors.lastname: Mejorado
authors.forename: Christophe
authors.initials: C
authors.lastname: Hoarau
authors.forename: Thomas R R
authors.initials: TR
authors.lastname: Pettus
mesh_terms: D006873:Hydroquinones / Q000737:chemistry*; D019344:Lactic Acid / Q000737:chemistry*; D015394:Molecular Structure; D012118:Resorcinols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006873:Hydroquinones; D012118:Resorcinols; D019344:Lactic Acid