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Yet, their stereocontrolled preparation remains challenging. Herein, we report a novel strategy towards versatile chiral\u2010at\u2010P alkenylphosphonamidates through a one\u2010pot Ni\u2010catalyzed C\u2212P coupling\/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. Remarkably, a chemo\u2010 and diastereodivergent behavior was observed upon subtle changes in the reaction conditions. Additionally, selective derivatizations of chiral alkenylphosphonamidates demonstrate their versatility as building blocks for the synthesis of structurally diverse P\u2010stereogenic compounds.<\/jats:p>","DOI":"10.1002\/anie.202307450","type":"journal-article","created":{"date-parts":[[2023,6,24]],"date-time":"2023-06-24T14:56:52Z","timestamp":1687618612000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["Asymmetric Synthesis of Chiral\u2010at\u2010P Alkenylphosphonamidates through Nickel\u2010Catalyzed C\u2212P Coupling of Phosphoramidites and Alkenyl Halides"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7463-7114","authenticated-orcid":false,"given":"Xiao\u2010Bing","family":"Chen","sequence":"first","affiliation":[{"name":"Stratingh Institute for Chemistry University of Groningen  Nijenborgh 4 9747\u2009AG Groningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3841-727X","authenticated-orcid":false,"given":"Dami\u00e1n","family":"Pad\u00edn","sequence":"additional","affiliation":[{"name":"Stratingh Institute for Chemistry University of Groningen  Nijenborgh 4 9747\u2009AG Groningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8432-4640","authenticated-orcid":false,"given":"Charlotte N.","family":"Stindt","sequence":"additional","affiliation":[{"name":"Stratingh Institute for Chemistry University of Groningen  Nijenborgh 4 9747\u2009AG Groningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0588-8435","authenticated-orcid":false,"given":"Ben L.","family":"Feringa","sequence":"additional","affiliation":[{"name":"Stratingh Institute for Chemistry University of Groningen  Nijenborgh 4 9747\u2009AG Groningen 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See ref.\u2005[24]."},{"key":"e_1_2_8_98_1","unstructured":"\u00a0"},{"key":"e_1_2_8_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar990084k"},{"key":"e_1_2_8_100_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904948"},{"key":"e_1_2_8_101_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.abc3183"},{"key":"e_1_2_8_102_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000124"},{"key":"e_1_2_8_103_1","unstructured":"Conversely Pd-catalyzed arylation of phosphoramidites tolerated the use of1\u2009das coupling partner."},{"key":"e_1_2_8_104_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00515a028"},{"key":"e_1_2_8_105_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja904197q"},{"key":"e_1_2_8_106_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature13274"},{"key":"e_1_2_8_107_1","unstructured":"Smaller substrates might also saturate the metal catalyst (or strongly bind to it) making the oxidative addition to the vinyl halide also more difficult. Further scrutiny of the reaction mechanism would be necessary to shed some light regarding these observations."},{"key":"e_1_2_8_108_1","unstructured":"The striking difference in reactivity observed betweenE-bromopropene and 2-bromopropene was again rationalized in terms of a slower reductive elimination with the former. The higher steric bulkiness offered by 2-bromopropene might accelerate the reductive elimination step."},{"key":"e_1_2_8_109_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00125B"},{"key":"e_1_2_8_110_1","unstructured":"A related phosphonium intermediate could also be detected in the Pd-catalyzed arylation of phosphoramidites albeit under different conditions. 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