{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T03:12:06Z","timestamp":1791429126959,"version":"4.3.3"},"reference-count":56,"publisher":"American Association for the Advancement of Science (AAAS)","issue":"6598","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Science"],"published-print":{"date-parts":[[2022,6,10]]},"abstract":"<jats:p>The stereoselective synthesis of molecules bearing stereogenic phosphorus(V) centers represents an enduring challenge in organic chemistry. Although stereospecific nucleophilic substitution at P(V) provides a general strategy for elaborating optically active P(V) compounds, existing methods for accessing the requisite chiral building blocks rely almost entirely on diastereocontrol using chiral auxiliaries. Catalytic, enantioselective methods for the synthesis of synthetically versatile stereogenic P(V) building blocks offer an alternative approach to stereogenic-at-P(V) targets without requiring stoichiometric quantities of chiral control elements. Here, we report an enantioselective hydrogen-bond-donor\u2013catalyzed synthesis of aryl chlorophosphonamidates and the development of these products as versatile chiral P(V) building blocks. We demonstrate that the two leaving groups on these chlorophosphonamidates can be displaced sequentially and stereospecifically to access a wide variety of stereogenic-at-P(V) compounds featuring diverse substitution patterns.<\/jats:p>","DOI":"10.1126\/science.abp8488","type":"journal-article","created":{"date-parts":[[2022,6,9]],"date-time":"2022-06-09T13:56:06Z","timestamp":1654782966000},"page":"1230-1236","source":"Crossref","is-referenced-by-count":130,"title":["Enantioselective hydrogen-bond-donor catalysis to access diverse stereogenic-at-P(V) compounds"],"prefix":"10.1126","volume":"376","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5654-6780","authenticated-orcid":true,"given":"Katherine C.","family":"Forbes","sequence":"first","affiliation":[{"name":"Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7952-3661","authenticated-orcid":true,"given":"Eric N.","family":"Jacobsen","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr5002035"},{"key":"e_1_3_2_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2003.09.015"},{"key":"e_1_3_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0103211"},{"key":"e_1_3_2_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2019.130819"},{"key":"e_1_3_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.9b02135"},{"key":"e_1_3_2_7_2","doi-asserted-by":"crossref","first-page":"1188","DOI":"10.1002\/chem.201805039","article-title":"Phosphorus versus sulfur: Discovery of benzenephosphonamidates as versatile sulfonamide-mimic chemotypes acting as carbonic anhydrase inhibitors","volume":"25","author":"Nocentini A.","year":"2019","unstructured":"A. Nocentini, P. Gratteri, C. T. Supuran, Phosphorus versus sulfur: Discovery of benzenephosphonamidates as versatile sulfonamide-mimic chemotypes acting as carbonic anhydrase inhibitors. Chemistry 25, 1188\u20131192 (2019). 30411821","journal-title":"Chemistry"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.49.5.1898-1906.2005"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.2183\/pjab.97.026"},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00031B"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.3390\/sym13050889"},{"key":"e_1_3_2_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2017.10.022"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2012.01.007"},{"key":"e_1_3_2_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.gresc.2020.12.002"},{"key":"e_1_3_2_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)99124-X"},{"key":"e_1_3_2_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)97063-1"},{"key":"e_1_3_2_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)90157-1"},{"key":"e_1_3_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja312352p"},{"key":"e_1_3_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00076a072"},{"key":"e_1_3_2_20_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aau3369"},{"key":"e_1_3_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b13898"},{"key":"e_1_3_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c00687"},{"key":"e_1_3_2_23_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-021-00697-9"},{"key":"e_1_3_2_24_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aam7936"},{"key":"e_1_3_2_25_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.abf4359"},{"key":"e_1_3_2_26_2","doi-asserted-by":"crossref","unstructured":"M. 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