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The novel strategy tolerates a wide range of <jats:italic>\u03b1<\/jats:italic>\u2010CF<jats:sub>3<\/jats:sub> alkynyl ketimines and <jats:italic>\u03b1<\/jats:italic>\u2010cyano ketones with both aryl and alkyl substitutents. A preliminary asymmetric synthesis of chiral product <jats:bold>3<\/jats:bold> has been attempted by using copper and chiral thiourea as the cocatalyst with excellent yields (86\u201099\u2009%) and good enantioselectivities (71\u201378\u2009% <jats:italic>ee<\/jats:italic>). Furthermore, product <jats:bold>3\u2009aa<\/jats:bold> could be obtained on a gram\u2010scale reaction with 75\u2009% yield and 99\u2009% <jats:italic>ee<\/jats:italic> after recrystallization. Several products were also transformed readily. Control experiments indicate that the reaction involves a process with a base\u2010catalyzed or chiral thiourea\u2010catalyzed Mannich\u2010type reaction followed by a highly regioselective copper\u2010catalyzed ring\u2010closing reaction on the alkynyl moiety in a 6<jats:italic>\u2010endo<\/jats:italic>\u2010<jats:italic>dig<\/jats:italic> fashion.<\/jats:p>","DOI":"10.1002\/chem.202200128","type":"journal-article","created":{"date-parts":[[2022,2,28]],"date-time":"2022-02-28T09:35:01Z","timestamp":1646040901000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Copper\u2010Catalyzed Regioselective [3+3] Annulations of Alkynyl Ketimines with <i>\u03b1<\/i>\u2010Cyano Ketones: the Synthesis of Polysubstituted 4<i>H<\/i>\u2010Pyran Derivatives with a CF<sub>3<\/sub>\u2010Containing Quaternary Center"],"prefix":"10.1002","volume":"28","author":[{"given":"Cheng","family":"Sheng","sequence":"first","affiliation":[{"name":"Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontier Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  800 Dongchuan Road Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zheng","family":"Ling","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontier Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  800 Dongchuan Road Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tanveer","family":"Ahmad","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontier Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  800 Dongchuan Road Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fang","family":"Xie","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontier Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  800 Dongchuan Road Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4788-4195","authenticated-orcid":false,"given":"Wanbin","family":"Zhang","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontier Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  800 Dongchuan Road Shanghai 200240 China"},{"name":"College of Chemistry Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,3,18]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"For the review see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300402y"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(00)00624-7"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np070256j"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm1009154"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm5012676"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b00008"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.11.055"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-020-71246-w"},{"key":"e_1_2_3_10_2","unstructured":"S. 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