Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202111778
Keywords
cascade reaction; chiral carboxylic acid; hydrocarboxylation; Nickel; transfer hydrogenation
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Funding
- National Natural Science Foundation of China [21927811, 21602126, 21675103, 21804081]
- Natural Science Foundation [ZR202102270004]
- Higher Educational Science and Technology Program of Shandong Province [J18KA077]
- Peking University Shenzhen Graduate School and Shenzhen Bay Laboratory
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A nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction was utilized to convert terminal alkynes to alpha-chiral carboxylic acids. The reaction showed high selectivity and efficiency in preparing biologically active compounds.
We report a stereoselective conversion of terminal alkynes to alpha-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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