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dc.contributor.authorMear, Sarah Jane
dc.contributor.authorJamison, Timothy F
dc.date.accessioned2020-06-23T19:32:09Z
dc.date.available2020-06-23T19:32:09Z
dc.date.issued2019-10
dc.identifier.issn1520-6904
dc.identifier.urihttps://hdl.handle.net/1721.1/125952
dc.description.abstractWe 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.en_US
dc.description.sponsorshipNational Science Foundation Graduate Research Fellowship Program (grant no. 1122374)en_US
dc.language.isoen
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionof10.1021/acs.joc.9b02630en_US
dc.rightsCreative Commons Attribution 4.0 International licenseen_US
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/en_US
dc.sourceACSen_US
dc.titleDiazotization of S-sulfonyl-cysteinesen_US
dc.typeArticleen_US
dc.identifier.citationMear, 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)en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.relation.journalJournal of Organic Chemistryen_US
dc.eprint.versionFinal published versionen_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dc.date.updated2019-12-18T18:06:51Z
dspace.date.submission2019-12-18T18:06:53Z
mit.journal.volume84en_US
mit.journal.issue22en_US


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