A reusable enantioselective catalytic system for the Kharasch-Sosnovsky allylic oxidation of alkenes based on a ditopic azabis(oxazoline) ligand

Aldea, Luis and Delso, Ignacio and Hager, Markus and Glos, Martin and Garcia, Jose I. and Mayoral, Jose A. and Reiser, Oliver (2012) A reusable enantioselective catalytic system for the Kharasch-Sosnovsky allylic oxidation of alkenes based on a ditopic azabis(oxazoline) ligand. TETRAHEDRON, 68 (17). pp. 3417-3422. ISSN 0040-4020,

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Abstract

An easily recoverable and reusable enantioselective catalytic system based on the self-assembly of a coordination polymer through the use of a chiral ditopic ligand, is described for the allylic oxidation of cycloalkenes with tert-butyl perbenzoate. Upon addition of the substrates and a coordinating solvent (acetone or acetonitrile) the coordination polymer disassembles, allowing the catalysis to take place in homogeneous phase. After completion of the reaction, the catalyst reassembles as a coordination polymer upon solvent evaporation and addition of hexane, and is recovered as an insoluble solid. This way, good enantioselectivities and yields are obtained in seven consecutive operation cycles. (C) 2011 Elsevier Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: OXAZOLINE-CONTAINING LIGANDS; CHARGE-TRANSFER COMPLEXES; TERT-BUTYL PERBENZOATE; ASYMMETRIC CATALYSIS; COORDINATION POLYMERS; NMR-SPECTROSCOPY; NONCOVALENT IMMOBILIZATION; FLUOROUS BIS(OXAZOLINES); COPPER(I) COMPLEXES; CHIRAL CATALYSTS; Copper catalysis; Bis(oxazoline) ligands; Allylic oxidation; Kharasch-Sosnovsky oxidation; Supported catalysts
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 May 2020 10:14
Last Modified: 14 May 2020 10:14
URI: https://pred.uni-regensburg.de/id/eprint/18864

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