Kinetic Resolution of Epoxides by a CC Bond-Forming Reaction: Highly Enantioselective Addition of Indoles to cis, trans, and meso Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes

Kinetic Resolution of Epoxides by a CC Bond-Forming Reaction: Highly Enantioselective Addition of Indoles to cis, trans, and meso Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes

The high reactivity of indoles has led to a new approach for the kinetic resolution of epoxides. [Cr(salen)] efficiently catalyzes a new CC bond‐forming reaction that allows the kinetic resolution of cis and trans aromatic epoxides (see scheme). By employing the same catalytic system, different ind...

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Veröffentlicht in:Angewandte Chemie International Edition 2004-01, Vol.43 (1), p.84-87
Hauptverfasser: Bandini, Marco, Cozzi, Pier Giorgio, Melchiorre, Paolo, Umani-Ronchi, Achille
Format: Artikel
Sprache:eng
Schlagworte:
aromatic epoxides
asymmetric catalysis
indoles
kinetic resolution
N,O ligands
O ligands
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Zusammenfassung:The high reactivity of indoles has led to a new approach for the kinetic resolution of epoxides. [Cr(salen)] efficiently catalyzes a new CC bond‐forming reaction that allows the kinetic resolution of cis and trans aromatic epoxides (see scheme). By employing the same catalytic system, different indolyl derivatives were obtained in high enantiomeric excesses (up to 98 %) by asymmetric ring opening of meso‐stilbene oxide.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352073