期刊
ACS CATALYSIS
卷 13, 期 21, 页码 14213-14220出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.3c04187
关键词
nickel; transfer hydrogenation; asymmetrichydrogenation; chiral carboxylic acids; hydrogenbonding
A chiral nickel complex was developed for catalyzing asymmetric transfer hydrogenation of alpha-substituted acrylic acids under mild conditions without high-pressure hydrogen gas. The method allows for the synthesis of chiral compounds, including beta-amino acids and alpha-methyl carboxylic acids, which are useful for the preparation of nonsteroidal anti-inflammatory drugs.
A chiral nickel complex that catalyzed asymmetric transfer hydrogenation of alpha-substituted acrylic acids under mild conditions and avoided the use of high-pressure hydrogen gas was developed. The products included chiral beta-amino acids and alpha-methyl carboxylic acids such as three nonsteroidal anti-inflammatory profens. Deuterium-labeling experiments and DFT studies pointed to an unconventional protonation of a metalacyclopropane complex formed by alpha-phenylacrylic acid which was hydrogen bonded with formic acid. An alternative conventional pathway of nickel hydride insertion cannot explain selective deuteration at beta-position of alpha-phenylacrylic acid when HCO2D was used.
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