ArticleAngewandte Chemie (International ed. in English)2016
Enantiospecific Alkynylation of Alkylboronic Esters.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 73 citations in OpenAlex.
- Article
- Stereoselective Construction of β-chiral Homoallyl Functionalities by Substrate- and Reagent-Controlled Iterative 1,2-Metallate Rearrangements.Organic letters · 2023Article
- Synthesis of 3-borylated cyclobutanols from epihalohydrins or epoxy alcohol derivatives.Chemical science · 2023Article
- Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes.Organic letters · 2022Article
- Lithium Enolate with a Lithium-Alkyne Interaction in the Enantioselective Construction of Quaternary Carbon Centers: Concise Synthesis of (+)-Goniomitine.Angewandte Chemie (International ed. in English) · 2022Article
- α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.Chemical science · 2022Article
- Enantioselective catalytic 1,2-boronate rearrangements.Science (New York, N.Y.) · 2021Article
- Studies on the Lithiation, Borylation, and 1,2-Metalate Rearrangement of O-Cycloalkyl 2,4,6-Triisopropylbenzoates.Angewandte Chemie (International ed. in English) · 2021Article
- Stereospecific 1,2-Migrations of Boronate Complexes Induced by Electrophiles.Angewandte Chemie (International ed. in English) · 2020Review
- Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes.Chemical science · 2020Article
- Desymmetrization of CChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Odd-even alternations in helical propensity of a homologous series of hydrocarbons.Nature chemistry · 2020Article
- Catalytic protodeboronation of pinacol boronic esters: formal anti-Markovnikov hydromethylation of alkenes.Chemical science · 2019Article
- Carbopalladation of C-C σ-bonds enabled by strained boronate complexes.Nature chemistry · 2019Article
- Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.Angewandte Chemie (International ed. in English) · 2019Article
- Iterative assembly line synthesis of polypropionates with full stereocontrol.Nature chemistry · 2017Article
- Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
- Selective uni- and bidirectional homologation of diborylmethane.Chemical science · 2017Article
- Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron "Ate" Complexes and C(spJournal of the American Chemical Society · 2017Article
- Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.Angewandte Chemie (International ed. in English) · 2017Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction. The process involves use of α-lithio vinyl bromide or vinyl carbamate species, for which application to Zweifel-type reactions has not previously been explored. The resulting functionalized 1,1-disubstituted alkenes undergo facile base-mediated elimination to generate terminal alkyne products in high yield and excellent levels of enantiospecificity over a wide range of pinacolboronic ester substrates. Furthermore, along with terminal alkynes, internal and silyl-protected alkynes can be formed by simply introducing a suitable carbon- or silicon-based electrophile after the base-mediated 1,2-elimination reaction.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.