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Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide\u2010phosphonium salt\u2010catalyzed regio\u2010 and stereoselective cascade reaction of readily available linear \u03b2,\u03b3\u2010unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio\u2010 and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone \u03b1\u2010addition followed by <jats:italic>O<\/jats:italic>\u2010participated substitution; and the multiple hydrogen\u2010bonding interactions between Br\u00f8nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.<\/jats:p>","DOI":"10.1002\/anie.202106046","type":"journal-article","created":{"date-parts":[[2021,7,2]],"date-time":"2021-07-02T10:40:25Z","timestamp":1625222425000},"page":"19860-19870","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":65,"title":["Regio\u2010 and Stereoselective Cascade of \u03b2,\u03b3\u2010Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro\u2010Fused [2,3\u2010b] Skeletons"],"prefix":"10.1002","volume":"60","author":[{"given":"Hongkui","family":"Zhang","sequence":"first","affiliation":[{"name":"Key Laboratory of Green Chemistry &amp; Technology of Ministry of Education College of Chemistry Sichuan University  29 Wangjiang Road Chengdu 610064 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiajia","family":"He","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry &amp; Technology of Ministry of Education College of Chemistry Sichuan University  29 Wangjiang Road Chengdu 610064 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yayun","family":"Chen","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry &amp; Technology of Ministry of Education College of Chemistry Sichuan University  29 Wangjiang Road Chengdu 610064 P. R. China"},{"name":"School of Environmental and Chemical Engineering Jiangsu University of Science and Technology  Zhenjiang 212003 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng","family":"Zhuang","sequence":"additional","affiliation":[{"name":"National Chengdu Center for Safety Evaluation of Drugs and National Clinical Research Center for Geriatrics West China Hospital Sichuan University  Chengdu 610064 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chunhui","family":"Jiang","sequence":"additional","affiliation":[{"name":"School of Environmental and Chemical Engineering Jiangsu University of Science and Technology  Zhenjiang 212003 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kai","family":"Xiao","sequence":"additional","affiliation":[{"name":"National Chengdu Center for Safety Evaluation of Drugs and National Clinical Research Center for Geriatrics West China Hospital Sichuan University  Chengdu 610064 P. R. 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selected reviews see:"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC02692J"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900211"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201600394"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700795"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.201900276"},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202001604"},{"key":"e_1_2_6_93_1","unstructured":"For selected examples by our group see:"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201900613"},{"key":"e_1_2_6_94_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201900613"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c01079"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0GC02134B"},{"key":"e_1_2_6_97_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-020-9754-7"},{"key":"e_1_2_6_98_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202102352"},{"key":"e_1_2_6_98_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202102352"},{"key":"e_1_2_6_99_1","unstructured":"See Table\u2005S1\u2013S3 in Supporting Information for more details."},{"key":"e_1_2_6_100_1","unstructured":"Deposition Numbers 202753 (for catalystP16) and 1966942 (for4i)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_6_101_1","unstructured":"See Table\u2005S6 S7 in Supporting Information for details of bioactivity study."},{"key":"e_1_2_6_102_1","unstructured":"See Figure\u2005S1\u2013S3 in Supporting Information for more details."},{"key":"e_1_2_6_103_1","unstructured":"Gaussian\u200909 Revision\u2009D.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Li X. Caricato H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005A. Montgomery J.\u2005J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Taroverov T. Keith R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M.\u2005N.\u2005C. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels O. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski D.\u2005J. Fox Gaussian Inc. Wallingford CT 2013."},{"key":"e_1_2_6_104_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_6_105_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_2_6_106_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21759"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202106046","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202106046","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202106046","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,20]],"date-time":"2023-08-20T14:33:23Z","timestamp":1692542003000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202106046"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,8,3]]},"references-count":123,"journal-issue":{"issue":"36","published-print":{"date-parts":[[2021,9]]}},"alternative-id":["10.1002\/anie.202106046"],"URL":"https:\/\/doi.org\/10.1002\/anie.202106046","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,8,3]]},"assertion":[{"value":"2021-05-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-08-03","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}