C-1-symmetric versus C-2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions

Fraile, Jose M. and Garcia, Jose I. and Gissibl, Anja and Mayoral, Jose A. and Pires, Elisabet and Reiser, Oliver and Roldan, Marta and Villalba, Isabel (2007) C-1-symmetric versus C-2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions. CHEMISTRY-A EUROPEAN JOURNAL, 13 (31). pp. 8830-8839. ISSN 0947-6539, 1521-3765

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Abstract

A thorough experimental and theoretical study of the enantioselective cyclopropanation of alkenes catalyzed by chiral bis(oxazoline)- and azabis(oxazoline)-copper complexes, which comprise a new family of ligands that lack C, symmetry, has been conducted. Surprisingly high enantioselectivities were observed with some of these ligands, which were rationalized on the basis of molecular modeling studies. The course of the asymmetric induction in connection with ligand symmetry and the implications for supported enantioselective catalysts are discussed.

Item Type: Article
Uncontrolled Keywords: COPPER-CATALYZED CYCLOPROPANATION; ASYMMETRIC-SYNTHESIS; CHIRAL BIS(OXAZOLINE); METAL-COMPLEXES; DIAZO-COMPOUNDS; MECHANISM; PYBOX; CYCLOADDITION; CARBENES; INSIGHTS; asymmetric catalysis; bis(oxazolines); computational mechanistic models; copper; cyclopropanation
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: 11 Jan 2021 10:52
Last Modified: 11 Jan 2021 10:52
URI: https://pred.uni-regensburg.de/id/eprint/33366

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