Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 32, Pages 7768-7776Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob01359g
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A family of chiral quaternary 3-aminooxindole butenolides has been synthesized by BINOL-derived phosphoric acid-catalyzed addition of trimethylsiloxyfuran to isatin-derived ketimines. Such a vinylogous Mannich-type reaction was found to produce diastereoisomeric butenolides in good yields and in most cases high enantiomeric excesses. The configurational assignment of the obtained products was safely performed by chemical correlation. A computational study of the transition state allowed rationalizing the obtained stereochemical outcome, highlighting the possible binding modes of the catalyst-iminenucleophile transition complex.
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