Abstract
Despite the importance of enantiopure chiral sulfoxides, few methods exist that allow for their deracemization. Here, we show that an enantiopure sulfoxide can be produced from the corresponding racemate using Viedma ripening involving rearrangement-induced racemization. The suitable candidate for Viedma ripening was identified from a library of 24 chiral sulfoxides through X-ray structure determination. Starting from the racemic sulfoxide, an unprecedented application of a 2,3-sigmatropic rearrangement type racemization in a Viedma ripening process allowed for complete deracemization.
Original language | English |
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Pages (from-to) | 4454-4457 |
Number of pages | 4 |
Journal | Crystal Growth and Design |
Volume | 17 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2 Aug 2017 |
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Dive into the research topics of 'Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening'. Together they form a unique fingerprint.Datasets
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CCDC 1528092: Experimental Crystal Structure Determination
Engwerda, A. H. J. (Contributor), Koning, N. (Contributor), Tinnemans, P. (Contributor), Meekes, H. (Contributor), Bickelhaupt, F. M. (Contributor), Rutjes, F. P. J. T. (Contributor) & Vlieg, E. (Contributor), Unknown Publisher, 2 Aug 2017
DOI: 10.5517/ccdc.csd.cc1n939c, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n939c&sid=DataCite
Dataset
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CCDC 1528095: Experimental Crystal Structure Determination
Engwerda, A. H. J. (Contributor), Koning, N. (Contributor), Tinnemans, P. (Contributor), Meekes, H. (Contributor), Bickelhaupt, F. M. (Contributor), Rutjes, F. P. J. T. (Contributor) & Vlieg, E. (Contributor), Unknown Publisher, 2 Aug 2017
DOI: 10.5517/ccdc.csd.cc1n93dg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n93dg&sid=DataCite
Dataset
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CCDC 1528096: Experimental Crystal Structure Determination
Engwerda, A. H. J. (Contributor), Koning, N. (Contributor), Tinnemans, P. (Contributor), Meekes, H. (Contributor), Bickelhaupt, F. M. (Contributor), Rutjes, F. P. J. T. (Contributor) & Vlieg, E. (Contributor), Unknown Publisher, 2 Aug 2017
DOI: 10.5517/ccdc.csd.cc1n93fh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n93fh&sid=DataCite
Dataset