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