Enantioselective Friedel-Crafts reaction of acylpyrroles with glyoxylates catalyzed by BINOL-Ti(IV) complexes |
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Authors: | Majer Jakub Kwiatkowski Piotr Jurczak Janusz |
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Institution: | Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland. |
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Abstract: | We report the first efficient enantioselective Friedel-Crafts hydroxyalkylation of pyrroles having one electron-withdrawing group at the α, β or N-positions with alkyl glyoxylates catalyzed by readily available chiral BINOL-Ti(IV) complexes (1-5 mol %). The reaction regioselectively led to the desired pyrrole-hydroxyacetic acid derivatives with good yields (70-96%) and enantiomeric excesses up to 96%, and is applicable in multigram scale with low loading of the catalyst (1 mol %). |
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