Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 219, Issue -, Pages 32-38Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2018.12.009
Keywords
Asymmetric synthesis; Enantioselective catalysis; Fluorine containing compounds; Fluoro-enolates; Michael additions
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Funding
- National Natural Science Foundation of China [21761132021, 21472082]
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This research presents the first example of catalytic enantioselective Michael addition reactions between 1-(1-(phenylsulfonyl)vinylsulfonyl)benzene and detrifluoroacetylatively in situ generated 3-fluorooxindole-derived enolates. The optimal catalyst includes Cu(OTf)(2) and (1S,2S)-1,2-diphenylethane-1,2-diamine featuring NHR functionalities. The reactions are conducted in THE at -20 degrees C using DIPEA as a base. The additions show reasonably high degree of structural generality and, therefore, synthetic value for preparation of a new family of compounds possessing pharmacophoric 3-fluorooxindole moiety, solofeaturing quaternary C-F stereogenic center.
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