A.H.J. Engwerda, N. Koning, P. Tinnemans, H. Meekes, F.M. Bickelhaupt, F.P.J.T. Rutjes, E. Vlieg,
Deracemization of a racemic allylic sulfoxide using Viedma ripening,
Cryst. Growth Des. 17 (2017) 4454-4457

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.