Influence of the conformation of salen complexes on the stereochemistry of the asymmetric epoxidation of olefins

Journal article


Publication Details

Author(s): Scheurer A, Maid H, Hampel F, Saalfrank R, Toupet L, Mosset P, Puchta R, van Eikema Hommes N
Journal: European Journal of Organic Chemistry
Publisher: Wiley-VCH Verlag
Publication year: 2005
Journal issue: 12
Pages range: 2566-2574
ISSN: 1434-193X


Abstract


Compared with Katsuki's or Jacobsen's catalysts (R,R,R,R)-1 or (R,R)-2, the phenomenon of reversed asymmetric induction in the course of the epoxidation of unfunctionalised olefins in the presence of (salen)manganese complex (S,S)-3 is indirectly explained by means of quantumchemical calculations, as well as by H-1 NMR spectra of salen ligand (S,S)-10 and diamagnetic low-spin nickel complex (S,S)-7 and by its X-ray structure analysis. Whereas in (R,R,R,R)-1 and (R,R)-2 the phenyl and cyclohexyl substituents occupy equatorial positions, the origin for the reversed enantioselection caused by manganese catalyst (S,S)-3, is based on an axial position of the acyclic heteroalkyl substituents in the diimine backbone of (S,S)-3 as exemplarily confirmed by model nickel complex (S,S)-7. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).



FAU Authors / FAU Editors

Hampel, Frank Dr.
Lehrstuhl für Organische Chemie I
Puchta, Ralph PD Dr.
Naturwissenschaftliche Fakultät
Saalfrank, Rolf Prof. Dr.
Naturwissenschaftliche Fakultät
Scheurer, Andreas Dr.
Lehrstuhl für Anorganische und Allgemeine Chemie
van Eikema Hommes, Nico Dr.
Computer-Chemie-Centrum


How to cite

APA:
Scheurer, A., Maid, H., Hampel, F., Saalfrank, R., Toupet, L., Mosset, P.,... van Eikema Hommes, N. (2005). Influence of the conformation of salen complexes on the stereochemistry of the asymmetric epoxidation of olefins. European Journal of Organic Chemistry, 12, 2566-2574. https://dx.doi.org/10.1002/ejoc.200500042

MLA:
Scheurer, Andreas, et al. "Influence of the conformation of salen complexes on the stereochemistry of the asymmetric epoxidation of olefins." European Journal of Organic Chemistry 12 (2005): 2566-2574.

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Last updated on 2018-15-07 at 01:10