title: Stereocontrolled approach to phenyl cyclitols from (SR)-[(p-tolylsulfinyl)methyl]-p-quinol.
abstract: Reactions of enantiopure (SR)-[(p-tolylsulfinyl)methyl]-p-quinol with ArAlMe(2) reagents allowed a highly diastereoselective 1,4-addition of the aryl group with an efficient desymmetrization of the prochiral cyclohexadienone moiety. The asymmetric synthesis of phenyl-substituted polyoxygenated cyclohexane derivatives was achieved by combining this reaction with a stereoselective reduction and elimination of the beta-hydroxysulfoxide, after oxidation to sulfone, to recover a carbonyl group, and a stereoselective epoxidation.
authors.affiliation: Departamento de Química Orgánica (C-I), Universidad Autónoma, Cantoblanco, 28049-Madrid, Spain.
authors.forename: Estíbaliz
authors.initials: E
authors.lastname: Merino
authors.forename: Rosanne P A
authors.initials: RP
authors.lastname: Melo
authors.forename: Montserrat
authors.initials: M
authors.lastname: Ortega-Guerra
authors.forename: María
authors.initials: M
authors.lastname: Ribagorda
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño