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Org Biomol Chem. 2013 Aug 28;11(32):5217-21. doi: 10.1039/c3ob41267a.

Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles.

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  • 1Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore.


An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine-thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.

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