title: Asymmetric aldol reaction catalyzed by the anion of an ionic liquid.
abstract: Herein we report the synthesis of a chiral imidazolium salt derived from trans-L-hydroxyproline and its applications as a catalyst for the asymmetric aldol reaction. By performing the aldol reaction in [Bmim]NTf(2) as a solvent, we report excellent isolated yields of the aldol product (up to 99%), as well as modest to excellent selectivities (dr superior to 99:1. ee up to 89%). Mechanistic insights and the origins of the selectivity of the aldol reaction are discussed on the basis of the results obtained with two catalytic imidazolium salts having different H-bonding potential.
authors.affiliation: Department of Chemistry, Université de Montréal, C.P. 6128 Succursale Centre-ville, Montréal, Québec, H3C 3J7, Canada.
authors.forename: Vincent
authors.initials: V
authors.lastname: Gauchot
authors.forename: Andreea R
authors.initials: AR
authors.lastname: Schmitzer