Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 9, Pages 2852-2856Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200903009
Keywords
annulation; asymmetric catalysis; molecular complexity; spiro compounds; tandem reactions
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Funding
- National Natural Science Foundation of China [20772084, 20972101]
- PCSIRTC [IRT0846]
- National Basic Research Program of China [2010CB833303]
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An efficient tandem reaction for the asymmetric synthesis of six-membered spirocyclic oxindoles has been successfully developed through a formal [2+ 2+2] annulation strategy. The amine-catalysed stereoselective Michael addition of aliphatic aldehydes to electron-deficient olefinic oxindole motifs gave chiral C3 components, which were further combined with diverse electrophiles (activated olefins or imines) to afford spirocyclic oxindoles with versatile molecular complexity (up to six contiguous stereogenic centres, high diastereo- and enantioselectivities).
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