Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 23, Pages 4165-4169Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701107
Keywords
Organocatalysis; Michael addition; 3,3'-bisindolines; organofluorines; green chemistry
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Funding
- NIH [GM106260]
- Georgetown Environment Initiative (GEI)
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A highly diastereoselective organocatalytic reaction for the synthesis of fluorinated 3,3'-bisindolines exhibiting adjacent tetrasubstituted carbon stereocenters is described. A broad variety of heterochiral bisindolines was prepared in 91-99% yield using 3-fluorooxindoles and isatylidene malononitriles in the presence of catalytic amounts of triethylamine in water or aqueous solution. The reaction can be upscaled without compromising yield and diastereoselectivity and the general usefulness of this method was demonstrated with various Michael acceptors and extended to aldol and Mannich reactions.
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