Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens |
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Authors: | Peng Yang Yaxin Sun Kaiyue Fu Li Zhang Guang Yang Jieyu Yue Yu Ma Jianrong Steve Zhou Bo Tang |
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Abstract: | We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716. |
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Keywords: | cascade reaction chiral carboxylic acid hydrocarboxylation Nickel transfer hydrogenation |
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