Issue 18, 2016
From the journal:

Organic & Biomolecular Chemistry

New biphenyl iminium salt catalysts for highly enantioselective asymmetric epoxidation: role of additional substitution and dihedral angle†

Philip C. Bulman Page,*a   Christopher J. Bartlett,a   Yohan Chan,a   Steven M. Allin,b   Michael J. McKenzie,c   Jérôme Lacourd  and  Garth A. Jonesa  

* Corresponding authors

a School of Chemistry, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, UK
E-mail: p.page@uea.ac.uk

b Department of Chemistry, Nottingham Trent University, Clifton, Nottinghamshire NG11 8NS, UK

c Charnwood Molecular Ltd, 7 Beaumont Court, Prince William Road, Loughborough, Leicestershire LE11 5GA, UK

d Département de Chimie Organique, Université de Genève, Quai Ernest Ansermet 30, CH-1121 Genève 4, Switzerland

Abstract

New biaryl iminium salt catalysts for enantioselective alkene epoxidation containing additional substitution in the heterocyclic ring are reported. The effects upon conformation and enantioselectivity of this additional substitution, and the influence of dihedral angle in these systems, has been investigated using a synthetic approach supported by density functional theory. Enantioselectivities of up to 97% ee were observed.

Graphical abstract: New biphenyl iminium salt catalysts for highly enantioselective asymmetric epoxidation: role of additional substitution and dihedral angle

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Article information

DOI
https://doi.org/10.1039/C6OB00542J
Article type
Paper
Submitted
11 Mar 2016
Accepted
15 Mar 2016
First published
16 Mar 2016
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2016,14, 4220-4232

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New biphenyl iminium salt catalysts for highly enantioselective asymmetric epoxidation: role of additional substitution and dihedral angle

P. C. Bulman Page, C. J. Bartlett, Y. Chan, S. M. Allin, M. J. McKenzie, J. Lacour and G. A. Jones, Org. Biomol. Chem., 2016, 14, 4220 DOI: 10.1039/C6OB00542J

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