A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions |
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Authors: | Zhuang Wei Poulsen Thomas B Jørgensen Karl Anker |
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Institution: | Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000, Aarhus C, Denmark. |
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Abstract: | Bis-sulfonamides are demonstrated to be promising candidates for the efficient activation of carbonyl compounds through hydrogen bonding. Exemplified by three carbonyl addition reactions: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions we show that bis-triflamides or bis-nonaflamides of commercially available chiral diamines act as chiral Br?nsted-acid catalysts, leading to the optically active products in moderate to excellent yields and with enantioselectivities up to 73% ee. |
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