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Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: use as catalysts in enantioselective asymmetric epoxidation.

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posted on 28.09.2015, 12:34 by Philip C. Bulman Page, Christopher A. Pearce, Yohan Chan, Phillip Parker, Benjamin Buckley, Gerasimos A. Rassias, Mark Elsegood
A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelective oxazolidine formation

Funding

This investigation has enjoyed the support of Loughborough University, the EPSRC, the University of East Anglia, and the ERDF (ISCE-Chem & INTERREG IVa programme 4061). We are indebted to the Royal Society for an Industry Fellowship (to PCBP) and the EPSRC national mass spectrometry service at the University of Wales, Swansea.

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  • Science

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  • Chemistry

Published in

Journal of Organic Chemistry

Citation

PAGE, P.C.B. ... et al, 2015. Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: use as catalysts in enantioselective asymmetric epoxidation. Journal of Organic Chemistry, 80 (16), pp. 8036-8045.

Publisher

© American Chemical Society

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2015

Notes

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.5b01157

ISSN

1520-6904

Language

en

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