Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 31, Pages 10817-10820Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602314
Keywords
asymmetric catalysis; chiral phosphoric acids; cycloaddition; kinetic resolution; organocatalysis
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Funding
- National Science Foundation [CHE-1300382]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1300382] Funding Source: National Science Foundation
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Under control of a chiral Bronsted acid catalyst, racemic indolines undergo intramolecular Povarov reactions with achiral aromatic aldehydes bearing a pendent dienophile. One enantiomer of the indoline reacts preferentially, resulting in the highly enantio-and diastereoselective formation of polycyclic heterocycles with four stereogenic centers. This kinetic resolution approach exploits the differential formation/reactivity of diastereomeric ion pairs.
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