title: InCl3-catalyzed regio- and stereoselective thiolysis of alpha,beta-epoxycarboxylic acids in water.
abstract: [reaction: see text] The thiolysis of alpha,beta-epoxycarboxylic acids 1a-e by thiols 2a,b is more efficient in water than in dichloromethane or SFC. At pH 9.0 phenylthiolate generally attacks the C-alpha carbon while at pH 4.0, and in the presence of InCl3 (10 mol %), the thiolysis is exclusively C-beta regioselective. In all cases, the processes are completely anti-diasteroselective, and the corresponding products 3, 4, and 5 have been isolated in good yields. Both water and catalysts have been recovered and reused.
authors.affiliation: Centro di Eccellenza Materiali Innovativi Nanostrutturati, Dipartimento di Chimica, Università di Perugia, Via Elce di Sotto 8, I-06123 Perugia, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Fringuelli
authors.forename: Ferdinando
authors.initials: F
authors.lastname: Pizzo
authors.forename: Simone
authors.initials: S
authors.lastname: Tortoioli
authors.forename: Luigi
authors.initials: L
authors.lastname: Vaccaro