Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 5, Pages 1747-1753Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203221
Keywords
asymmetric synthesis; cascade reactions; organocatalysis; spiro compounds; synthetic methods
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Funding
- National Basic Research Program of China (973 Program) [2010CB833300]
- State Key Laboratory of Elemento-Organic Chemistry
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Bispirooxindole derivatives containing three stereocenters, including two spiro quaternary centers, were synthesized in a high-yielding, atypically rapid, and stereocontrolled cascade Michaelcyclization reaction between methyleneindolinones and isothiocyanato oxindoles catalyzed by a bi- or multifunctional organocatalyst. Mild conditions were used to construct bispirooxindoles with excellent enantio- and diastereomeric purities within less than 1 min. Catalyst reconfiguration offered access to the opposite enantiomer. This exceptionally highly efficient procedure will allow diversity-oriented syntheses of this intriguing class of compounds with potential biological activities.
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