Diazotization of S-sulfonyl-cysteines
Name
acs.joc.9b02630.pdf
Description
Published version
Size
1.47 MB
Format
Adobe PDF
Checksum (MD5)
0607efd91830cf22f4afac875b846d68
Author(s)
Mear, Sarah Jane
Jamison, Timothy F
Date Issued
October 2019
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution 4.0 International license
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DOI of Published Version
https://doi.org/10.1021/acs.joc.9b02630
