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This protocol, consisting of a bifunctional iminophosphorane (BIMP) catalyzed nucleophilic desymmetrization of prochiral, bench stable P(V) precursors and subsequent enantiospecific substitution allows for divergent access to a wide range of\n                    <jats:italic>C<\/jats:italic>\n                    \u2010,\n                    <jats:italic>N<\/jats:italic>\n                    \u2010,\n                    <jats:italic>O<\/jats:italic>\n                    \u2010 and\n                    <jats:italic>S<\/jats:italic>\n                    \u2010 substituted P(V) containing compounds from a handful of enantioenriched intermediates. A new ureidopeptide BIMP catalyst\/thiaziolidinone leaving group combination allowed for a far wider substrate scope and increased reaction efficiency and practicality over previously established protocols. The resulting enantioenriched intermediates could then be transformed into an even greater range of distinct classes of P(V) compounds by displacement of the remaining leaving group as well as allowing for even further diversification downstream. Density functional theory (DFT) calculations were performed to pinpoint the origin of enantioselectivity for the BIMP\u2010catalyzed desymmetrization, to rationalize how a superior catalyst\/leaving group combination leads to increased generality in our second\u2010generation catalytic system, as well as shed light onto observed stereochemical retention and inversion pathways when performing late\u2010stage enantiospecific S\n                    <jats:sub>\n                      <jats:italic>N<\/jats:italic>\n                    <\/jats:sub>\n                    2@P reactions with Grignard reagents.\n                  <\/jats:p>","DOI":"10.1002\/anie.202400673","type":"journal-article","created":{"date-parts":[[2024,2,21]],"date-time":"2024-02-21T11:58:21Z","timestamp":1708516701000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":50,"title":["Second Generation Catalytic Enantioselective Nucleophilic Desymmetrization at Phosphorus (V): Improved Generality, Efficiency and Modularity"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3641-7281","authenticated-orcid":false,"given":"Michele","family":"Formica","sequence":"first","affiliation":[{"name":"Department of Chemistry, Chemistry Research Laboratory University of Oxford  12 Mansfield Road OX1 3TA Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8841-1239","authenticated-orcid":false,"given":"Branislav","family":"Ferko","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Chemistry Research Laboratory University of Oxford  12 Mansfield Road OX1 3TA Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas","family":"Marsh","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Chemistry Research Laboratory University of Oxford  12 Mansfield Road OX1 3TA Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0633-2634","authenticated-orcid":false,"given":"Timothy A.","family":"Davidson","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Chemistry Research Laboratory University of Oxford  12 Mansfield Road OX1 3TA Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2039-4321","authenticated-orcid":false,"given":"Ken","family":"Yamazaki","sequence":"additional","affiliation":[{"name":"Division of Applied Chemistry Okayama University, Tsushimanaka  Okayama 700-8530 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2456-5236","authenticated-orcid":false,"given":"Darren J.","family":"Dixon","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Chemistry Research Laboratory University of Oxford  12 Mansfield Road OX1 3TA Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,3,27]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201800693"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b00734"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2015.11.009"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature17180"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(20)31022-9"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1503\/cmaj.060068"},{"key":"e_1_2_8_7_1","unstructured":"World Health Organization Medicines.World Heal. 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