Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

Anthonius H. J. Engwerda, Niels Koning, Paul Tinnemans, Hugo Meekes*, F. Matthias Bickelhaupt, Floris P. J. T. Rutjes, Elias Vlieg

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review


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 languageEnglish
Pages (from-to)4454-4457
Number of pages4
JournalCrystal Growth and Design
Issue number8
Publication statusPublished - 2 Aug 2017


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