{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T19:02:49Z","timestamp":1787166169297,"version":"build-2736575974"},"reference-count":34,"publisher":"Wiley","issue":"48","license":[{"start":{"date-parts":[[2024,10,11]],"date-time":"2024-10-11T00:00:00Z","timestamp":1728604800000},"content-version":"am","delay-in-days":354,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2023,10,23]],"date-time":"2023-10-23T00:00:00Z","timestamp":1698019200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE-1900299"],"award-info":[{"award-number":["CHE-1900299"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["S10 OD021758-01A1"],"award-info":[{"award-number":["S10 OD021758-01A1"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2023,11,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A copper\u2010catalyzed dearomative alkynylation of pyridines is reported with excellent regio\u2010 and enantioselectivities. The synthetically valuable enantioenriched 2\u2010alkynyl\u20101,2\u2010dihydropyridine products afforded are generated from the readily available feedstock, pyridine, and commercially available terminal alkynes. The three\u2010component reaction between a pyridine, a terminal alkyne, and methyl chloroformate employs copper chloride and StackPhos, a chiral biaryl\n                    <jats:italic>P<\/jats:italic>\n                    ,\n                    <jats:italic>N\u2010<\/jats:italic>\n                    ligand, as the catalytic system. Under mild reaction conditions, the desired 1,2\u2010addition products are delivered in up to 99\u2009% yield with regioselectivity ratios up to 25\u2009:\u20091 and enantioselectivities values of up to 99\u2009% ee. Activated and non\u2010activated terminal alkynes containing a wide range of functional groups are well tolerated. Even acetylene gas delivered mono\u2010alkynylated products in high yield and ee. Application of the methodology in an efficient enantioselective synthesis of the chiral piperidine indolizidine, coniceine, is reported.\n                  <\/jats:p>","DOI":"10.1002\/anie.202312967","type":"journal-article","created":{"date-parts":[[2023,10,11]],"date-time":"2023-10-11T16:34:52Z","timestamp":1697042092000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Enantio\u2010 and Regioselective Copper\u2010Catalyzed 1,2\u2010Dearomatization of Pyridines"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1515-9455","authenticated-orcid":false,"given":"Mukesh","family":"Pappoppula","sequence":"first","affiliation":[{"name":"Department of Chemistry and Florida Center for Heterocyclic Compounds University of Florida  P.O. Box 117200 Gainesville FL 32611 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kathryn L.","family":"Olsen","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Florida Center for Heterocyclic Compounds University of Florida  P.O. Box 117200 Gainesville FL 32611 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7808-9549","authenticated-orcid":false,"given":"Devin R.","family":"Ketelboeter","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Florida Center for Heterocyclic Compounds University of Florida  P.O. Box 117200 Gainesville FL 32611 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4576-638X","authenticated-orcid":false,"given":"Aaron","family":"Aponick","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Florida Center for Heterocyclic Compounds University of Florida  P.O. 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