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

Philip Bulman Page, Christopher Bartlett, Yohan Chan, Steven Allin, Michael McKenzie, Jérôme Lacour, Garth Jones

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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.
Original languageEnglish
Pages (from-to)4220-4232
Number of pages13
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number18
Early online date16 Mar 2016
DOIs
Publication statusPublished - 14 May 2016

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