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Kinetic Resolution of Epoxides by a CC Bond‐Forming Reaction: Highly Enantioselective Addition of Indoles to cis , trans , and meso Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes
Author(s) -
Bandini Marco,
Cozzi Pier Giorgio,
Melchiorre Paolo,
UmaniRonchi Achille
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352073
Subject(s) - kinetic resolution , enantioselective synthesis , chemistry , catalysis , reactivity (psychology) , enantiomer , ring (chemistry) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology
The high reactivity of indoles has led to a new approach for the kinetic resolution of epoxides. [Cr(salen)] efficiently catalyzes a new CC 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.