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Although great advances have been made in the construction of achiral double-allylation reagents, the catalytic enantioselective synthesis and application of linear 1,3-bifunctional allylborons remain rarely developed. Herein, we report a copper-catalyzed enantio-, regio-, and E\/Z-selective hydroboration of 1,3-dienylsilanes to afford bifunctional allylation reagents bearing a chiral center at the allylic position. The kinetic resolution process of the E\/Z-mixture of dienylsilanes ensures high ee of products regardless of the initial E\/Z-ratio. Density functional theory (DFT) studies were conducted to probe the origins of the enantio- and E\/Z-selectivities. Sequential allylation of aldehydes with the newly developed double-allylation reagents can construct chiral 3,6-dihydropyrans and pent-2-ene-1,5-diols bearing four contiguous stereocenters with excellent diastereoselectivities and enantioselectivities.<\/jats:p>","DOI":"10.1021\/jacs.6c16251","type":"journal-article","created":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T20:01:29Z","timestamp":1791230489000},"page":"45071-45081","source":"Crossref","is-referenced-by-count":0,"title":["Enantio-,\nRegio-, and\n                    <i>E<\/i>\n                    -Selective Hydroboration\nof 1,3-Dienylsilanes to Construct\nBifunctional Allylation Reagents"],"prefix":"10.1021","volume":"148","author":[{"given":"Wenqing","family":"Ti","sequence":"first","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiuyu","family":"Li","sequence":"additional","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiajun","family":"Lu","sequence":"additional","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yixiao","family":"Li","sequence":"additional","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5786-4537","authenticated-orcid":true,"given":"Aijun","family":"Lin","sequence":"additional","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0348-5405","authenticated-orcid":true,"given":"Peng","family":"Sun","sequence":"additional","affiliation":[{"name":"China Academy of Chinese Medical Sciences , , ,","place":["Beijing, China, 100700"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4865-820X","authenticated-orcid":true,"given":"Hequan","family":"Yao","sequence":"additional","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8166-5503","authenticated-orcid":true,"given":"Shang","family":"Gao","sequence":"additional","affiliation":[{"name":"China Pharmaceutical University , , ,","place":["Nanjing, China, 210009"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"key":"2026102111080144700_cit1a","doi-asserted-by":"publisher","first-page":"301","DOI":"10.1038\/s41570-021-00266-5","article-title":"Bifunctional\nreagents in organic synthesis","volume":"5","author":"Huang","year":"2021","journal-title":"Nat. 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