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Herein, catalytic asymmetric conjugate 1,6\u2010, 1,8\u2010 and 1,10\u2010borylation was developed with excellent regioselectivity, which delivered \u03b1\u2010chiral boronates in moderate to high yields with high enantioselectivity. The produced chiral boronate smoothly underwent oxidation, cross\u2010coupling, and one\u2010carbon homologation to give synthetically versatile chiral compounds in moderate yields with excellent stereoretention. Furthermore, a stereomechanistic analysis was conducted using DFT calculations, which provides insights into the origins of the regioselectivity. Finally, the present 1,6\u2010borylation was successfully applied in an efficient one\u2010pot asymmetric synthesis of (\u2212)\u20107,8\u2010dihydrokavain.<\/jats:p>","DOI":"10.1002\/anie.202016081","type":"journal-article","created":{"date-parts":[[2021,2,6]],"date-time":"2021-02-06T08:27:06Z","timestamp":1612600026000},"page":"9493-9499","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Copper(I)\u2010Catalyzed Asymmetric Conjugate 1,6\u2010, 1,8\u2010, and 1,10\u2010Borylation"],"prefix":"10.1002","volume":"60","author":[{"given":"Chang\u2010Yun","family":"Shi","sequence":"first","affiliation":[{"name":"CAS Key Laboratory of Synthetic Chemistry of Natural Substances Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road Shanghai 200032 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