Localized partitioning of enantiomers in solid samples of sulfoxides: importance of sampling method in determination of enantiopurity

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Localized partitioning of enantiomers in solid samples of sulfoxides: importance of sampling method in determination of enantiopurity

Flynn, Aaran J.; Ford, Alan; Maguire, Anita R.
Date: 2020-07-02
Copyright: © 2020 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in The 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 https://pubs.acs.org/doi/10.1021/acs.joc.0c01094
Related: https://pubs.acs.org/doi/10.1021/acs.joc.0c01094
Full text restriction information: Access to this article is restricted until 12 months after publication by request of the publisher
Restriction lift date: 2021-07-02
Citation: Flynn, A. J., Ford, A. and Maguire, A. R. (2020) 'Localized Partitioning of Enantiomers in Solid Samples of Sulfoxides: Importance of Sampling Method in Determination of Enantiopurity', The Journal of Organic Chemistry, 85(15), pp. 10216-10221. doi: 10.1021/acs.joc.0c01094
Published Version: 10.1021/acs.joc.0c01094

Abstract:

Localized partitioning of amorphous enantioenriched aryl benzyl sulfoxides in the solid state can lead to substantial variation in enantiopurities, even for sulfoxides which do not show detectable levels of self-disproportionation of enantiomers (SDE) during chromatography on an achiral stationary phase. The importance of preparation of representative samples of enantioenriched sulfoxides for chiral HPLC to enable reproducible results is clear.

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