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Here, we report the development of a copper\u2010catalyzed enantioselective 1,4\u2010hydropyridylation of conjugated dienes. Utilizing 2\u2010fluoropyridine as the electrophile, CuOAc, and the chiral ligand Tol\u2010BINAP, we optimized reaction conditions to achieve the desired chiral 1,1\u2010diaryl products containing both a pyridine and a cis\u2010crotyl group. Mechanistic studies and DFT calculations revealed that the 1,2\u2010hydrocupration step is enantio\u2010determining, and the concerted nucleophilic aromatic substitution proceeds via six\u2010membered cyclic transition states.<\/jats:p>","DOI":"10.1002\/anie.202420918","type":"journal-article","created":{"date-parts":[[2024,11,26]],"date-time":"2024-11-26T22:40:01Z","timestamp":1732660801000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Copper\u2010Catalyzed Regioselective and Enantioselective Hydropyridylation of Dienes for the Synthesis of Chiral Diaryl Compounds via Concerted Nucleophilic Aromatic Substitution"],"prefix":"10.1002","volume":"64","author":[{"given":"Minjeong","family":"Seo","sequence":"first","affiliation":[{"name":"Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST)  Daejeon 34141 Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sanghyup","family":"Seo","sequence":"additional","affiliation":[{"name":"Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST)  Daejeon 34141 Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joonho","family":"Jung","sequence":"additional","affiliation":[{"name":"Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST)  Daejeon 34141 Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5030-9610","authenticated-orcid":false,"given":"Hyunwoo","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST)  Daejeon 34141 Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,12,5]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For relevant reviews:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3md00088e"},{"key":"e_1_2_7_4_1","unstructured":"For selected examples:"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b00518"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm900933k"},{"key":"e_1_2_7_7_1","unstructured":"For selected examples of functionalization \u03c0-unsaturated compound with pyridine:"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c03056"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-33452-0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-29462-7"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c04043"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c04486"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC05621A"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03998"},{"key":"e_1_2_7_15_2","doi-asserted-by":"crossref","unstructured":"G. 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