title: Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with sulfur nucleophiles.
abstract: The synthesis of 2-sulfanyl-1,2-dihydro-naphthalen-1-ols is described. This methodology is based on rhodium catalysis and enables various thiols to undergo an asymmetric SN2' ring opening of oxabenzonorbornadiene. Under the reaction conditions ([Rh(COD)Cl](2) (2.5 mol %), (S)-(R)-PPF-P(t)Bu(2) (6 mol %), AgOTf (7 mol %), NH(4)I (1.7 equiv), galvinoxyl (5 mol %), THF, 85 degrees C), aryl- and alkyl-sulfide adducts are obtained in good to excellent yield and in high enantiomeric excess (>90% ee).
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
authors.forename: Paul
authors.initials: P
authors.lastname: Leong
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens