Enantioselective catalysis; 150: Chiral-at-metal (eta(6)-p-cymene)ruthenium(II) complexes of binaphthyl ligands - Synthesis, characterization, and enantioselective catalysis

Brunner, Henri and Henning, Frauke and Weber, Matthias and Zabel, Manfred and Carmona, Daniel and Lahoz, Fernando J. (2003) Enantioselective catalysis; 150: Chiral-at-metal (eta(6)-p-cymene)ruthenium(II) complexes of binaphthyl ligands - Synthesis, characterization, and enantioselective catalysis. SYNTHESIS-STUTTGART (7). pp. 1091-1099. ISSN 0039-7881

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Abstract

Neutral and cationic half-sandwich (mu(6)-p-cymene)ruthenium complexes 9-12 with chiral Schiff base ligands derived from binaphthylamino derivatives and salicylaldehyde, diphenyl(2-formylphenyl)phosphane, and 2-pyridinealdehyde form two diastereomers which only differ in the metal configuration. From the diastereomeric mixtures of compounds 10 and 12 the major diastereomers crystallize, whereas for compound 9 both diastereomers co-crystallize in a 1: 1 ratio in the same single crystal. In compounds 13 and 14 containing the reduced Schiff base ligands, the nitrogen atom of the secondary amine functionality becomes another chiral center. In solution at room temperature the various diastereomers interconvert rapidly. The new compounds were used as catalysts in the enantioselective transfer hydrogenation of acetophenone with 2-propanol and in the Diels-Alder reaction of cyclopentadiene with methacrolein.

Item Type: Article
Uncontrolled Keywords: TRANSFER HYDROGENATION; OPTICAL RESOLUTION; CRYSTAL-STRUCTURE; TITANIUM; enantioselectivity; catalysis; ruthenium half-sandwich complexes; 1,1 '-binaphthyl ligands; chiral imines
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: 11 Aug 2021 06:47
Last Modified: 11 Aug 2021 06:47
URI: https://pred.uni-regensburg.de/id/eprint/39104

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