Journal
ACS CATALYSIS
Volume 9, Issue 2, Pages 791-797Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04654
Keywords
cooperative catalysis; enamine catalysis; Pd(II) catalysis; ketone; unactivated olefin; asymmetric hydroalkylation
Categories
Funding
- Chinese Academy of Science [XDB20020000]
- NSFC [21831007]
- STIC [JCYJ20170412150343516]
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Amine/Pd(II) cooperative catalysis has enabled a highly enantioselective addition of cyclic ketones to unactivated alkenes. The hallmark of the strategy includes amide-directed, regioselective activation of alkenes by Pd(II) and enhancing the nucleophilicity of alpha-carbon of the ketones by enamine catalysis to synergistically drive the reaction, which is basically unable to be accessed by a single catalyst. The combination of a commercially available Pd(II) catalyst and diphenylprolinol was able to provide the gamma-addition products with good to high yields and efficient stereochemical control (up to 95% ee).
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