期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 16, 页码 7328-7333出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c02075
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资金
- NSFC [21772148, 21971198]
- Wuhan University (WHU)
Chiral nitriles are valuable molecules in modern organic synthesis and drug discovery. Selectively differentiating the two nitrile groups of widely available malononitrile derivatives is a straightforward yet underdeveloped route to construct enantioenriched nitriles. Here we report an enantioselective nickel-catalyzed desymmetrization of malononitriles for the generation of nitrile-containing all-carbon quaternary stereocenters. This protocol involves a nickel-catalyzed addition of aryl boronic acids to alkynes, followed by a selective nitrile insertion, providing unprecedented access to enantioenriched 5-7-membered alpha-cyanocycloenones with a fully substituted olefin from a broad range of substrates. The synthetic utility of these nitrile products is demonstrated by gram-scale synthesis and conversion to several useful functional groups.
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