Brunner, Henri and Kagan, Henri B. and Kreutzer, Georg (2003) Asymmetric catalysis. Part 153: Metal-catalysed enantioselective alpha-ketol rearrangement. TETRAHEDRON-ASYMMETRY, 14 (15). pp. 2177-2187. ISSN 0957-4166
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Promoted by catalytic amounts of Ni complexes tertiary alpha-hydroxyketones 1a, 3a-5a undergo rearrangement, forming chiral isomers 1b, 3b-5b. The best enantioselection was obtained with the model system 1-benzoylcyclopentanol 4a/2-hydroxy-2-phenylcyclohexanone 4b. In a ligand screening 2-[4-(S)-tert-butyloxazolin-2-yl]pyridine gave the highest enantiomeric excess of 46% (S)-4b. The analogous isomerisation reactions of alpha-hydroxyimines 6a, 7a forming chiral alpha-aminoketones 6b, 7b were established. (C) 2003 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | COMPLEXES; CHIRALITY; LIGANDS; BENZYL; ACIDS; |
| 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: | 05 Aug 2021 05:44 |
| Last Modified: | 05 Aug 2021 05:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/38801 |
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