ArticleJournal of the American Chemical Society2009
Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Asymmetric dihydroboration of allenes enabled by ligand relay catalysis.Nature communications · 2024Article
- Direct, Mild, and General n-BuOrganic letters · 2017Article
- Highly selective olefin-assisted palladium-catalyzed oxidative carbocyclizationChemical science · 2017Article
- Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenes to Cyclobutenes.Angewandte Chemie (International ed. in English) · 2016Article
- Chelation-assisted substrate-controlled asymmetric lithiation-allylboration of chiral carbamate 1,2,4-butanetriol acetonide.Molecules (Basel, Switzerland) · 2015Article
- Article
- Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.Journal of the American Chemical Society · 2013Article
- Article
- Article
- Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.Journal of the American Chemical Society · 2013Article
- Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.Organic letters · 2013Article
- Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.Organic letters · 2012Article
- Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.Journal of the American Chemical Society · 2012Article
- Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.Tetrahedron · 2011Article
- Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.Journal of the American Chemical Society · 2011Article
- Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.Organic letters · 2011Article
- Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.Organic letters · 2011Article
- Enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers using a cross-metathesis allylboration sequence.Organic letters · 2010Article
- Chiral Brønsted acid-catalyzed allylboration of aldehydes.Journal of the American Chemical Society · 2010Article
- Enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols via aldehyde allylboration using alpha-stannylallylboranes generated by allene hydroboration followed by a highly diastereoselective 1,3-boratropic shift.Journal of the American Chemical Society · 2010Article
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4 authors.
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Abstract
Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-gamma-(substituted)allylboranes 9 and 15a-d. These allylboranes undergo highly diastereo- (> or = 90: 10) and enantioselective (typically 89-96% e.e.) allylboration reactions with representative aldehydes to give syn-beta-functionalized homoallylic alcohols.
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