ArticleJournal of the American Chemical Society2019
Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented Synthesis.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 42 citations in OpenAlex.
- Copper-catalyzed enantioselective allylation of cyclic anhydrides for generation of multiple chiral centers.Nature communications · 2026Article
- Review
- Sterically Stabilized Homoleptic Copper and Gold Allyl Complexes.Organometallics · 2026Article
- Desilylative allylation of 3,3-borylsilylpropene under metallaphotoredox catalysis.Nature communications · 2026Article
- Diversity-Oriented Method Development: Multifunctional Homoallylic Amines and Azabicyclooctanes Bearing a Bridgehead Enamine.Journal of the American Chemical Society · 2025Article
- Regio- and enantioselective synthesis of acyclic quaternary carbons via organocatalytic addition of organoborates to (Z)-Enediketones.Nature communications · 2024Article
- Copper-catalyzed yne-allylic substitutions: concept and recent developments.Beilstein journal of organic chemistry · 2024Review
- Copper-Catalyzed Enantioselective Borylative Allyl-Allyl Coupling of Allenes and AllylicACS catalysis · 2023Article
- Fused Tricyclic Guanidine Alkaloids: Insights into Their Structure, Synthesis and Bioactivity.Marine drugs · 2022Review
- Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.Angewandte Chemie (International ed. in English) · 2022Article
- Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Diastereo-, Enantio-, andOrganic letters · 2020Article
- Sulfonate N-Heterocyclic Carbene-Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C-C, C-B, C-H, and C-Si Bonds.Angewandte Chemie (International ed. in English) · 2020Review
- Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.Chemical science · 2020Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Synthesis of complex bioactive molecules is substantially facilitated by transformations that efficiently and stereoselectively generate polyfunctional compounds. Designing such processes is hardly straightforward, however, especially when the desired route runs counter to the inherently favored reactivity profiles. Furthermore, in addition to being efficient and stereoselective, it is crucial that the products generated can be easily and stereodivergently modified. Here, we introduce a catalytic process that delivers versatile and otherwise difficult-to-access organoboron entities by combining an allenylboronate, a hydride, and an allylic phosphate. Two unique selectivity problems had to be solved: avoiding rapid side reaction of a Cu-H complex with an allylic phosphate, while promoting its addition to an allenylboronate as opposed to the commonly utilized boron-copper exchange. The utility of the approach is demonstrated by applications to concise preparation of the linear fragment of pumiliotoxin B (myotonic, cardiotonic) and enantioselective synthesis and structure confirmation of netamine C, a member of a family of anti-tumor and anti-malarial natural products. Completion of the latter routes required the following noteworthy developments: (1) a two-step all-catalytic sequence for conversion of a terminal alkene to a monosubstituted alkyne; (2) a catalytic S
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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.