title: Enantioselective ruthenium-catalyzed 1,3-dipolar cycloadditions between C-carboalkoxy ketonitrones and methacrolein: solvent effect on reaction selectivity and its rational.
abstract: A catalytic 1,3-dipolar cycloaddition between carboalkoxy ketonitrones and methacrolein under the effect of chiral ruthenium Lewis acid (R,R-1) was developed with high regio-, diastereo-, and enantiocontrol. The diastereochemical outcome of the cycloaddition reaction is marked by a significant solvent effect, and a divergent endo or exo control can be tuned by an appropriate choice of both the solvent and the N- and O-substituents of the ketonitrone. A rationale of the solvent effect, based on the computational study of the interactions between the methacrolein-Ru complex and its counteranion (SbF6(-)), is proposed to explain the selectivities obtained.
authors.affiliation: LUNAM Université du Maine, Institut Molécules et Matériaux du Mans , UMR 6283 CNRS, Faculté des Sciences, 72085 Le Mans, Cedex 9, France.
authors.forename: Khalid B
authors.initials: KB
authors.lastname: Selim
authors.forename: Arnaud
authors.initials: A
authors.lastname: Martel
authors.forename: Mathieu Y
authors.initials: MY
authors.lastname: Laurent
authors.forename: Jérôme
authors.initials: J
authors.lastname: Lhoste
authors.forename: Sandrine
authors.initials: S
authors.lastname: Py
authors.forename: Gilles
authors.initials: G
authors.lastname: Dujardin