Deracemization of a racemic allylic sulfoxide using viedma ripening
| Autor: | Floris P. J. T. Rutjes, Paul Tinnemans, Niels Koning, F. Matthias Bickelhaupt, Anthonius H. J. Engwerda, Hugo Meekes, Elias Vlieg |
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| Přispěvatelé: | Theoretical Chemistry, AIMMS |
| Rok vydání: | 2017 |
| Předmět: |
Allylic rearrangement
010405 organic chemistry Sulfoxide Ripening General Chemistry Solid State Chemistry Synthetic Organic Chemistry 010402 general chemistry Condensed Matter Physics 01 natural sciences Article 0104 chemical sciences chemistry.chemical_compound Enantiopure drug chemistry Organic chemistry General Materials Science Theoretical Chemistry SDG 6 - Clean Water and Sanitation Racemization GeneralLiterature_REFERENCE(e.g. dictionaries encyclopedias glossaries) |
| Zdroj: | Crystal Growth & Design, 17, 8, pp. 4454-4457 Engwerda, A H J, Koning, N, Tinnemans, P, Meekes, H, Bickelhaupt, F M, Rutjes, F P J T & Vlieg, E 2017, ' Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening ', Crystal Growth and Design, vol. 17, no. 8, pp. 4454-4457 . https://doi.org/10.1021/acs.cgd.7b00828 Crystal Growth & Design, 17, 4454-4457 Crystal Growth & Design Crystal Growth and Design, 17(8), 4454-4457. American Chemical Society |
| ISSN: | 1528-7483 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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