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

Scheurer A, Maid H, Hampel F, Saalfrank R, Toupet L, Mosset P, Puchta R, van Eikema Hommes N (2005)

Publication Status: Published

Publication Type: Journal article

Publication year: 2005

Journal

Publisher: Wiley-VCH Verlag

Pages Range: 2566-2574

Journal Issue: 12

DOI: 10.1002/ejoc.200500042

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).

Authors with CRIS profile

Involved external institutions

Université de Rennes 1 / University of Rennes 1 France (FR)

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://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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