Further insight into the mechanism of Heck oxyarylation in the presence of chiral ligands

Kiss, Loránd and Kurtan, Tibor and Antus, Sandor and Brunner, Henri (2003) Further insight into the mechanism of Heck oxyarylation in the presence of chiral ligands. ARKIVOC (Part V). pp. 69-76. ISSN 1551-7012

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Abstract

The Heck oxyarylation reaction to 3-benzyloxypterocarpan (15) has been studied in the presence of chiral phosphine ligands, a chiral ionic liquid and (+)-alpha.pinene. The observed small selectivities suggest that this reaction takes place through parallel pathways and the main pathway involves an achiral intermediate 11 where the chirality introduced by the chiral ligands is lost. Although practical asymmetric Heck oxyarylation to chiral pterocarpans could not be achieved, a convenient Heck-oxyarylation synthesis of rac-15 with (+)-alpha.pinene as ligand gave the highest yield reported to this type of reactions.

Item Type: Article
Uncontrolled Keywords: EFFICIENT SYNTHESIS; A-I; PALLADIUM; CATALYSIS; PTEROCARPANS; DERIVATIVES; CYCLIZATION; COMPLEXES; pterocarpan; asymmetric Heck oxyarylation; ionic liquid; chiral ligand
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner
Depositing User: Dr. Gernot Deinzer
Date Deposited: 24 Aug 2021 13:45
Last Modified: 24 Aug 2021 13:45
URI: https://pred.uni-regensburg.de/id/eprint/39388

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