Engwerda Anthonius H J, Koning Niels, Tinnemans Paul, Meekes Hugo, Bickelhaupt F Matthias, Rutjes Floris P J T, Vlieg Elias
Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling, VU University, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
Cryst Growth Des. 2017 Aug 2;17(8):4454-4457. doi: 10.1021/acs.cgd.7b00828. Epub 2017 Jul 3.
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.
尽管对映体纯的手性亚砜很重要，但实现其消旋化的方法却很少。在此，我们表明，使用涉及重排诱导消旋化的维德马熟化法，可以从相应的外消旋体中制备出对映体纯的亚砜。通过X射线结构测定，从24种手性亚砜的文库中筛选出了适合维德马熟化的候选物。以外消旋亚砜为起始原料，在维德马熟化过程中前所未有的应用2,3-σ迁移重排型消旋化反应，实现了完全消旋化。
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