{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T02:32:35Z","timestamp":1760236355133,"version":"build-2065373602"},"reference-count":56,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2021,11,15]],"date-time":"2021-11-15T00:00:00Z","timestamp":1636934400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"The Ministry of Science and Higher Education","award":["N N204 445240"],"award-info":[{"award-number":["N N204 445240"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The resolution of racemic 1-phenylphosphin-2-en-4-one 1-oxide (2), was achieved through the fractional crystallization of its diastereomeric complexes with (4R,5R)-(\u2212)-2,2-dimethyl -\u03b1,\u03b1,\u03b1\u2032,\u03b1\u2032-tetraphenyl-dioxolan-4,5-dimethanol (R,R-TADDOL) followed by the liberation of the individual enantiomers of 2 by flash chromatography on silica gel columns. The resolution process furnished the two enantiomers of 2 of 99.1 and 99.9% e.e. at isolated yields of 62 and 59% (counted for the single enantiomer), respectively. The absolute configurations of the two enantiomers were established by means of X-ray crystallography of their diastereomerically pure complexes, i.e., (R)-2\u2022R,R)-TADDOL and (S)-2\u2022(R,R)-TADDOL. The structural analysis revealed that in the (R)-2\u2022(R,R)-TADDOL complex, the P-phenyl substituent occupied a pseudoequatorial position, whereas in (S)-2\u2022(R,R)-TADDOL, it appeared in both the pseudoequatorial and the pseudoaxial positions in four symmetrically independent molecules. Concurrent conformational changes of the TADDOL molecules were best described by the observed changes of a pseudo-torsional CO...OC angle that could be considered as a possible measure of TADDOL conformation in its receptor\u2013ligand complexes. The structural analysis of the (R,R)-TADDOL molecule revealed that efficiency of this compound for use as an effective resolving factor comes from its ability to flexibly fit its structure to both enantiomers of a ligand molecule, producing a rare case of resolution for both pure enantiomers with one chiral separating agent. The resolved (R)-2 was used to assign the absolute configuration of a recently described (\u2212)-1-phenylphosphin-2-en-4-one 1-sulfide by chemical correlation. In addition, an attempted stereoretentive reduction of (R)-2 by PhSiH3 at 60 \u00b0C revealed an unexpectedly low barrier for P-inversion in 1-phenylphosphin-2-en-4-one.<\/jats:p>","DOI":"10.3390\/molecules26226873","type":"journal-article","created":{"date-parts":[[2021,11,15]],"date-time":"2021-11-15T08:19:20Z","timestamp":1636964360000},"page":"6873","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Resolution of P-Sterogenic 1-Phenylphosphin-2-en-4-one 1-Oxide into Two Enantiomers by (R,R)-TADDOL and Conformational Diversity of the Phosphinenone Ring and TADDOL in the Crystal State"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6546-1519","authenticated-orcid":false,"given":"El\u017cbieta","family":"\u0141astawiecka","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33, 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Adam","family":"W\u0142odarczyk","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33, 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anna E.","family":"Kozio\u0142","sequence":"additional","affiliation":[{"name":"Department of Crystallography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Maria Curie-Sklodowska sq. 3, 20-031 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hanna","family":"Ma\u0142uszy\u0144ska","sequence":"additional","affiliation":[{"name":"Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0969-4689","authenticated-orcid":false,"given":"K. Micha\u0142","family":"Pietrusiewicz","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33, 20-614 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Grabulosa, A. (2011). P-Stereogenic Ligands in Enantioselective Catalysis, RSC Publishing. [1st ed.].","DOI":"10.1039\/9781849732703"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Kamer, P.C.J., and van Leeuwen, P.W.N.M. (2012). 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