Access to Enantioenriched 1,n ‐Diols by Cu‐Catalyzed Enantioselective Protoboration and Hydroboration of Alkenyl Ethers

Article Article scientifique Article Access to Enantioenriched 1,n ‐Diols by Cu‐Catalyzed Enantioselective Protoboration and Hydroboration of Alkenyl Ethers eng 2025-03-04 author Flaget Arthur 0000-0001-8757-8304 Department of Organic Chemistry University of Geneva Quai Ernest Ansermet 30 CH-1211 Geneva Switzerland 948106 author Cesa Orlando Jamiro Jon-Allie Department of Organic Chemistry University of Geneva Quai Ernest Ansermet 30 CH-1211 Geneva Switzerland 881565 Département de chimie physique (CHIFI) author Mazet Clement 0000-0002-2385-280X Department of Organic Chemistry University of Geneva Quai Ernest Ansermet 30 CH-1211 Geneva Switzerland 667534 Département de chimie organique (CHIOR) e202500009 10.1002/hlca.202500009 0018-019X https://onlinelibrary.wiley.com/doi/10.1002/hlca.202500009 We report two catalytic enantioselective borylation/oxidation sequences that streamline access to either enantioenriched 1,2‐ or 1,3‐diols starting from O ‐benzyl‐protected allylic alcohols as a single precursor. The approach takes advantage of the complementary regioselectivity of the Cu‐catalyzed protoboration and the Cu‐catalyzed hydroboration of disubstituted alkenes, which effectively install a borane function and a hydrogen atom on opposite C(sp 2 ) carbon atoms of a carbon–carbon double bond. The two methods feature broad substrate scope and are amenable to large scale without measurable loss of the catalytic efficiency. Both protocols display high levels of regioselectivity and enantioselectivity. Dewey 540 Swiss National Science Foundation Increasing molecular complexity by selective catalysis 188490 CH Projects 36 Département de chimie organique 141 false 763 Groupe Mazet Helvetica chimica acta 4f396467-39cf-497a-9642-f0ab599b6e3c Article (Published version) Public file.pdf 8873663 application/pdf 74bc0e36ec54a540bd2c0257c4cbf57f1a2462eefaf02dea3c74a3fcb418ae4a Vignette Public TOC.jpg 100398 image/png openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Access to Enantioenriched 1,n ‐Diols by Cu‐Catalyzed Enantioselective Protoboration and Hydroboration of Alkenyl Ethers	Helvetica chimica acta			2025	45	29

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Cesa, Orlando Jamiro Jon-Allie