title: Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes
abstract: A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.
authors.affiliation: Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Extremadura, Badajoz, Spain. mavalos@unex.es
authors.initials: M
authors.lastname: Avalos
authors.initials: R
authors.lastname: Babiano
authors.initials: P
authors.lastname: Cintas
authors.initials: FR
authors.lastname: Clemente
authors.initials: R
authors.lastname: Gordillo
authors.initials: JL
authors.lastname: Jimenez
authors.initials: JC
authors.lastname: Palacios
authors.initials: PR
authors.lastname: Raithby