ArticleJournal of the American Chemical Society2013
Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes.ACS catalysis · 2022Article
- Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters.Journal of the American Chemical Society · 2022Article
- Ruthenium-catalysed multicomponent synthesis of the 1,3-dienyl-6-oxy polyketide motif.Nature chemistry · 2020Article
- Ligand-controlled cobalt-catalyzed regiodivergent hydroboration of aryl,alkyl-disubstituted internal allenes.Chemical science · 2020Article
- Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.Chemical science · 2018Article
- Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles.Journal of the American Chemical Society · 2017Article
- Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.Angewandte Chemie (International ed. in English) · 2016Article
- Catalytic Borylative Opening of Propargyl Cyclopropane, Epoxide, Aziridine, and Oxetane Substrates: Ligand Controlled Synthesis of Allenyl Boronates and Alkenyl Diboronates.Angewandte Chemie (International ed. in English) · 2016Article
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2 authors.
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Abstract
Kinetically controlled hydroboration of allenylboronate 5 followed by double allylboration with the resulting allylborane (Z)-7 gave (Z)-2-methyl-1,5-anti-pentenediols 6 in good yield and high enantioselectivity in the presence of 10% BF3·OEt2 as the catalyst in the second allylboration step. Under thermodynamically controlled isomerization conditions, (Z)-7 can readily isomerize to (E)-7. Double allylboration of representative aldehydes with allylborane (E)-7 gave (E)-2-methyl-1,5-anti-pentenediols 4 in good yield and high enantioselectivity without requiring use of the BF3·OEt2 catalyst. Thus, 2-methyl-1,5-anti-pentenediols with either olefin geometry can be synthesized from the same allenylboronate precursor 5. Furthermore, 1,5-pentenediols 4 and 6 can be easily converted to 1,3,5-triols with excellent diastereoselectivity in one step.
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