ArticleAngewandte Chemie (International ed. in English)2019
Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 92 citations in OpenAlex.
- Force-modulated and strain-dependent stereoselectivity of copper-catalyzed reductive coupling.Chemical science · 2026Article
- Copper-catalyzed enantioselective allylation of cyclic anhydrides for generation of multiple chiral centers.Nature communications · 2026Article
- Asymmetric Ketone Diene Coupling via Stereodivergent Copper Catalysis.Journal of the American Chemical Society · 2026Article
- Enantioselective Syntheses of Secondary Alkylboronates via Asymmetric Regioselective Reduction of 1,3-Dienylboronates.Angewandte Chemie (International ed. in English) · 2026Article
- Kinetics and Mechanism of Enantioselective Cu-Catalyzed Alcohol Silylation.Journal of the American Chemical Society · 2025Article
- Preparation of 1,4-Diamines by Enantio- and Diastereoselective Cu-Josiphos-Catalyzed Reductive Couplings of Azatrienes and Imines: Regiodivergence Enabled by Catalyst Structure and Reagent Tailoring.Journal of the American Chemical Society · 2025Article
- Copper-Catalyzed Diastereo-, Enantio-, and (Journal of the American Chemical Society · 2024Article
- Organophosphates as Versatile Substrates in Organic Synthesis.Molecules (Basel, Switzerland) · 2024Review
- Copper-Catalyzed Asymmetric Acylboration of 1,3-Butadienylboronate with Acyl Fluorides.Angewandte Chemie (International ed. in English) · 2023Article
- Nickel-Catalyzed Enantioselective Coupling of Aldehydes and Electron-Deficient 1,3-Dienes Following an Inverse Regiochemical Course.Journal of the American Chemical Society · 2022Article
- Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation.Journal of the American Chemical Society · 2022Article
- Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.Journal of the American Chemical Society · 2022Article
- Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol.Angewandte Chemie (International ed. in English) · 2022Article
- A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.Organic letters · 2021Article
- 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
- Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.Organic letters · 2021Article
- Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles.Organic letters · 2021Article
- Diastereo-, Enantio-, andOrganic letters · 2020Article
- CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.Accounts of chemical research · 2020Article
- Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.Advanced synthesis & catalysis · 2020Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Recently, CuH-catalyzed reductive coupling processes involving carbonyl compounds and imines have become attractive alternatives to traditional methods for stereoselective addition because of their ability to use readily accessible and stable olefins as surrogates for organometallic nucleophiles. However, the inability to use aldehydes, which usually reduce too rapidly in the presence of copper hydride complexes to be viable substrates, has been a major limitation. Shown here is that by exploiting relative concentration effects through kinetic control, this intrinsic reactivity can be inverted and the reductive coupling of 1,3-dienes with aldehydes achieved. Using this method, both aromatic and aliphatic aldehydes can be transformed into synthetically valuable homoallylic alcohols with high levels of diastereo- and enantioselectivities, and in the presence of many useful functional groups. Furthermore, using a combination of theoretical (DFT) and experimental methods, important mechanistic features of this reaction related to stereo- and chemoselectivities were uncovered.
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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.