{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T23:40:13Z","timestamp":1773013213990,"version":"3.50.1"},"reference-count":24,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2021,1,7]],"date-time":"2021-01-07T00:00:00Z","timestamp":1609977600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003407","name":"Ministero dell\u2019Istruzione, dell\u2019Universit\u00e0 e della Ricerca","doi-asserted-by":"publisher","award":["PRIN 2017 \u201cSURSUMCAT\u201d"],"award-info":[{"award-number":["PRIN 2017 \u201cSURSUMCAT\u201d"]}],"id":[{"id":"10.13039\/501100003407","id-type":"DOI","asserted-by":"publisher"}]},{"name":"ITN-EID project Marie Sklodowska-Curie Actions","award":["- TECHNOTRAIN H2020-MSCA-ITN-2018 Grant Agreement 812944."],"award-info":[{"award-number":["- TECHNOTRAIN H2020-MSCA-ITN-2018 Grant Agreement 812944."]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>The development of new and efficient methods, reagents, and catalysts for the introduction of fluorine atoms or fluorinated moieties in molecular scaffolds has become a topic of paramount importance in organic synthesis. In this framework, the incorporation of the SCF3 group into organic molecule has often led to beneficial effects on the drug\u2019s metabolic stability and bioavailability. Here we report our studies aimed to the stereoselective synthesis of chiral \u03b1-SCF3-\u03b2\u2212ketoesters featuring a tetrasubstituted stereocenter. The use of a chiral auxiliary was crucial to synthesize enantiopure enamines that were reacted with N-trifluoromethylthio saccharin or phthalimide, to afford enantioenriched \u03b1-SCF3-tetrasubstitued \u03b2-keto esters. By using a readily available, inexpensive chiral diamine, such as trans-1,2-diaminocyclohexane, the fluorinated products could be obtained in modest to good yields, and, after the removal of the chiral auxiliary, \u03b1-substituted- \u03b1 trifluoromethylthio-\u03b2\u2212ketoesters were isolated with high enantioselectivity (up to 91% ee).<\/jats:p>","DOI":"10.3390\/sym13010092","type":"journal-article","created":{"date-parts":[[2021,1,7]],"date-time":"2021-01-07T02:33:29Z","timestamp":1609986809000},"page":"92","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Stereoselective Synthesis of Chiral \u03b1-SCF3-\u03b2-Ketoesters Featuring a Quaternary Stereocenter"],"prefix":"10.3390","volume":"13","author":[{"given":"Monica Fiorenza","family":"Boselli","sequence":"first","affiliation":[{"name":"Dipartimento di Chimica, Universit\u00e0 degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chiara","family":"Faverio","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica, Universit\u00e0 degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elisabetta","family":"Massolo","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica, Universit\u00e0 degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Laura","family":"Raimondi","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica, Universit\u00e0 degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8581-8009","authenticated-orcid":false,"given":"Alessandra","family":"Puglisi","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica, Universit\u00e0 degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9568-9642","authenticated-orcid":false,"given":"Maurizio","family":"Benaglia","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica, Universit\u00e0 degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1021\/acs.chemrev.5b00392","article-title":"Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II\u2013III, Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas","volume":"116","author":"Zhou","year":"2016","journal-title":"Chem. 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