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Herein, by using siloxypropadienes as the precursors of allyl copper(I) species, a copper(I)\u2010catalyzed diastereoselective and enantioselective reductive allylation of ketones was achieved, providing both <jats:italic>syn<\/jats:italic>\u2010diols and <jats:italic>anti<\/jats:italic>\u2010diols in good to excellent enantioselectivity. DFT calculations show that <jats:italic>cis<\/jats:italic>\u2010\u03b3\u2010siloxy\u2010allyl copper species are generated favorably with either 1\u2010TBSO\u2010propadiene or 1\u2010TIPSO\u2010propadiene. Moreover, the steric difference of TBS group and TIPS group distinguishes the face selectivity of acetophenone, leading to <jats:italic>syn<\/jats:italic>\u2010selectivity for 1\u2010TBSO\u2010propadiene and <jats:italic>anti<\/jats:italic>\u2010selectivity for 1\u2010TIPSO\u2010propadiene. Easy transformations of the products were performed, demonstrating the synthetic utility of the present method. Moreover, one chiral diol prepared in the above transformations was used as a suitable organocatalyst for the catalytic asymmetric reductive self\u2010coupling of aldimines generated <jats:italic>in situ<\/jats:italic> with B<jats:sub>2<\/jats:sub>(neo)<jats:sub>2<\/jats:sub>.<\/jats:p>","DOI":"10.1002\/anie.202402195","type":"journal-article","created":{"date-parts":[[2024,2,27]],"date-time":"2024-02-27T07:39:34Z","timestamp":1709019574000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Asymmetric Synthesis of Trisubstituted Vicinal Diols through Copper(I)\u2010Catalyzed Diastereoselective and Enantioselective Allylation of Ketones with Siloxypropadienes"],"prefix":"10.1002","volume":"63","author":[{"given":"Nan","family":"Jiang","sequence":"first","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pei\u2010Zhi","family":"Liu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry and Tianjin Key Laboratory of Biosensing and Molecular Recognition College of Chemistry Nankai University  94 Weijin Road Tianjin 300071 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhi\u2010Zhou","family":"Pan","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Si\u2010Qing","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qian","family":"Peng","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry and Tianjin Key Laboratory of Biosensing and Molecular Recognition College of Chemistry Nankai University  94 Weijin Road Tianjin 300071 China"},{"name":"Haihe Laboratory of Sustainable Chemical Transformations  Tianjin 300192 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9604-5198","authenticated-orcid":false,"given":"Liang","family":"Yin","sequence":"additional","affiliation":[{"name":"Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences  345 Lingling Road Shanghai 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