{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T11:36:54Z","timestamp":1760441814661,"version":"build-2065373602"},"reference-count":48,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2024,1,5]],"date-time":"2024-01-05T00:00:00Z","timestamp":1704412800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>This paper presents the general synthesis of a comprehensive group of P-chiral phosphinyl derivatives with a natural coumarin-type motif. A chiral substituent was attached at the third position of the coumarin molecule via the Knoevenagel procedure using readily available P-chiral phoshinylacetic acid esters without loss of enantiomeric purity. The application of salicylaldehyde-based derivatives allowed the incorporation of substituents of different electron character into the backbone of these coumarins making them suitable for subsequent chemical modifications. As a result, we gained access to six achiral (2a\u2013g) and a large number ((Sp)-4a\u2013f, (Sp)-6a\u2013e and (Rp)-8a) of new potential chiral ligand precursors, pharmaceuticals, etc. with an imbedded phosphinyl group with evidenced biological activity based on the natural coumarin backbone. The molecular structure, including absolute configuration, was determined for seven compounds.<\/jats:p>","DOI":"10.3390\/sym16010073","type":"journal-article","created":{"date-parts":[[2024,1,5]],"date-time":"2024-01-05T05:12:17Z","timestamp":1704431537000},"page":"73","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis and Structural Elucidation of P-stereogenic Coumarins"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8833-3170","authenticated-orcid":false,"given":"Kamil F.","family":"Dziuba","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry and Crystallochemistry, Institute of Chemical Sciences, Faculty of Chemistry, Marie Curie-Sk\u0142odowska University in Lublin, 33 Gliniana St., 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S\u0142awomir","family":"Frynas","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Crystallochemistry, Institute of Chemical Sciences, Faculty of Chemistry, Marie Curie-Sk\u0142odowska University in Lublin, 33 Gliniana St., 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anna E.","family":"Kozio\u0142","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Crystallochemistry, Institute of Chemical Sciences, Faculty of Chemistry, Marie Curie-Sk\u0142odowska University in Lublin, 33 Gliniana St., 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8292-7373","authenticated-orcid":false,"given":"Katarzyna","family":"Szwaczko","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Crystallochemistry, Institute of Chemical Sciences, Faculty of Chemistry, Marie Curie-Sk\u0142odowska University in Lublin, 33 Gliniana St., 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1039\/JS8682100053","article-title":"On the artificial production of coumarin and formation of its homologues","volume":"21","author":"Perkin","year":"1868","journal-title":"J. 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