期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 2, 页码 574-584出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02676
关键词
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资金
- National Natural Science Foundation of China [U1804283, 81903465]
- National Postdoctoral Program for Innovative Talents [BX201700071]
- China Postdoctoral Science Foundation [2017M622348]
- Central Plains Scholars and Scientists Studio Fund [2018002]
An efficient organocatalytic asymmetric Michael addition of 4-substituted-pyrazol-5-ones to beta-trifluoromethyl-alpha,beta-unsaturated ketones was developed. In the presence of a dipeptide-based urea-amide tertiary amine catalyst, an array of chiral products containing pyrazolone and trifluoromethyl moieties bearing vicinal quaternary and tertiary stereocenters were obtained in good yields with good to excellent enantioselectivity and diastereoselectivity (up to 95% yields, up to 97% ee, and >20:1 d.r.). Moreover, the reaction was compatible with 4-substituted-pyrazol-5-ones containing either aryl or alkyl group at the C3 position.
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