| dc.contributor.author | Mear, Sarah Jane | |
| dc.contributor.author | Jamison, Timothy F | |
| dc.date.accessioned | 2020-06-23T19:32:09Z | |
| dc.date.available | 2020-06-23T19:32:09Z | |
| dc.date.issued | 2019-10 | |
| dc.identifier.issn | 1520-6904 | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/125952 | |
| dc.description.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. | en_US |
| dc.description.sponsorship | National Science Foundation Graduate Research Fellowship Program (grant no. 1122374) | en_US |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | 10.1021/acs.joc.9b02630 | en_US |
| dc.rights | Creative Commons Attribution 4.0 International license | en_US |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | en_US |
| dc.source | ACS | en_US |
| dc.title | Diazotization of S-sulfonyl-cysteines | en_US |
| dc.type | Article | en_US |
| dc.identifier.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) | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.relation.journal | Journal of Organic Chemistry | en_US |
| dc.eprint.version | Final published version | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dc.date.updated | 2019-12-18T18:06:51Z | |
| dspace.date.submission | 2019-12-18T18:06:53Z | |
| mit.journal.volume | 84 | en_US |
| mit.journal.issue | 22 | en_US |
| mit.metadata.status | Complete | |
