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Diazotization of S-sulfonyl-cysteines

Author(s)
Mear, Sarah Jane; Jamison, Timothy F
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Creative Commons Attribution 4.0 International license https://creativecommons.org/licenses/by/4.0/
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Abstract
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 22 factorial design of experiment, highlighting the unique reactivity of cysteine derivatives in comparison with aliphatic amino acids.
Date issued
2019-10
URI
https://hdl.handle.net/1721.1/125952
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Mear, Sarah Jane, and Timothy F. Jamison, "Diazotization of S-sulfonyl-cysteines." Journal of Organic Chemistry 84, 22 (Oct. 2019): p. 15001-07 doi 10.1021/acs.joc.9b02630 ©2019 Author(s)
Version: Final published version
ISSN
1520-6904

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