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Diazotization of S-Sulfonyl-cysteines
[Image: see text] We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur’s nucleophilici...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2019
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6862327/ https://www.ncbi.nlm.nih.gov/pubmed/31657562 http://dx.doi.org/10.1021/acs.joc.9b02630 |
| Sumario: | [Image: see text] We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur’s nucleophilicity by the anomeric effect. The key transformation was optimized by a 2(2) factorial design of experiment, highlighting the unique reactivity of cysteine derivatives in comparison with aliphatic amino acids. |
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