ArticleNature chemistry2014
Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy.
Article in Nature chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 109 citations in OpenAlex.
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- In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I/Li-Exchange.Angewandte Chemie (International ed. in English) · 2023Article
- Anthranilamide-protected vinylboronic acid: rational monomer design for improved polymerization/transformation ability providing access to conventionally inaccessible copolymers.Chemical science · 2022Article
- Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides.Journal of the American Chemical Society · 2022Article
- Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates.Journal of the American Chemical Society · 2022Article
- Three-component 1,2-carboamination of vinyl boronic estersChemical science · 2021Article
- Chemical Synthesis of Cell Wall Constituents ofChemical reviews · 2021Review
- Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.Organic letters · 2021Article
- Solvation Effects on the Structure and Stability of Alkali Metal Carbenoids.Angewandte Chemie (International ed. in English) · 2021Article
- Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents.Journal of the American Chemical Society · 2019Article
- Catalytic protodeboronation of pinacol boronic esters: formal anti-Markovnikov hydromethylation of alkenes.Chemical science · 2019Article
- Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb "Amine".ChemSusChem · 2019Article
- CD1b Tetramers Identify T Cells that Recognize Natural and Synthetic Diacylated Sulfoglycolipids from Mycobacterium tuberculosis.Cell chemical biology · 2018Article
- Enantiospecific Three-Component Alkylation of Furan and Indole.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Synthesis of α-Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes.Angewandte Chemie (International ed. in English) · 2018Article
- Stereocontrolled Total Synthesis of (-)-Stemaphylline.Angewandte Chemie (International ed. in English) · 2017Article
- Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.Angewandte Chemie (International ed. in English) · 2017Article
- Iterative reactions of transient boronic acids enable sequential C-C bond formation.Nature chemistry · 2016Article
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2 authors at 1 institution in 1 country.
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Abstract
In planning organic syntheses, disconnections are most often made adjacent to functional groups, which assist in C-C bond formation. For molecules devoid of obvious functional groups this approach presents a problem, and so functionalities must be installed temporarily and then removed. Here we present a traceless strategy for organic synthesis that uses a boronic ester as such a group in a one-pot lithiation-borylation-protodeboronation sequence. To realize this strategy, we developed a methodology for the protodeboronation of alkyl pinacol boronic esters that involves the formation of a boronate complex with a nucleophile followed by oxidation with Mn(OAc)3 in the presence of the hydrogen-atom donor 4-tert-butylcatechol. Iterative lithiation-borylation-protodeboronation allows the coupling of smaller fragments to build-up long alkyl chains. We employed this strategy in the synthesis of hydroxyphthioceranic acid, a key component of the cell-wall lipid of the virulent Mycobacterium tuberculosis, in just 14 steps (longest linear sequence) with full stereocontrol.
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