Combining proline and ‘click chemistry’: a class of versatile organocatalysts for the highly diastereo- and enantioselective Michael addition in water |
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Institution: | 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China;2. Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, PR China |
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Abstract: | Based on ‘click chemistry’ conditions, a class of novel, facile, versatile pyrrolidine-based triazole derivatives were prepared, and proved to be efficient catalysts for the highly diastereoselective and enantioselective Michael addition of ketones to nitroalkenes. The Cu(I)-catalyzed 1,3-dipolar ‘click’ azide–alkyne cycloaddition provides modular and tunable features for the pyrrolidine-based triazole organocatalysts, and the resulting triazole moiety can serve as a phase tag to complete the reaction in water with an excellent yield and high enantiomeric excess. |
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