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Issue 18, 2016
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New biphenyl iminium salt catalysts for highly enantioselective asymmetric epoxidation: role of additional substitution and dihedral angle

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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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Supplementary files

Article information


Submitted
11 Mar 2016
Accepted
15 Mar 2016
First published
16 Mar 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 4220-4232
Article type
Paper
Author version available

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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