Asymmetric aldol reaction catalyzed by the anion of an ionic liquid
Vincent Gauchot1, Andreea R Schmitzer
1Department of Chemistry, Université de Montréal, C.P. 6128 Succursale Centre-ville, Montréal, Québec, H3C 3J7, Canada.
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.
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