Subtopic Deep Dive
Atroposelective Suzuki-Miyaura Coupling
Research Guide
What is Atroposelective Suzuki-Miyaura Coupling?
Atroposelective Suzuki-Miyaura coupling employs chiral ligands and catalysts to form axially chiral biaryls through enantioselective cross-coupling of aryl boronic acids and halides.
This method targets hindered biaryls with restricted rotation for axial chirality. Key advances include atropodiastereoselective couplings in natural product syntheses (Yalcouye et al., 2014). Over 10 papers since 2006 detail ligand designs and condition optimizations, with Wallace (2006) cited 165 times.
Why It Matters
Atroposelective Suzuki-Miyaura coupling enables synthesis of chiral biaryls in pharmaceuticals like ancistrotanzanine B (Bringmann et al., 2004) and materials with axial chirality. It scales to complex targets such as (–)-steganone via biaryl formation (Yalcouye et al., 2014). Applications extend to complestatin macrocycles using Pd-mediated couplings (Shimamura et al., 2010).
Key Research Challenges
Ligand Design for Hindered Biaryls
Developing chiral ligands that control selectivity in couplings of ortho-substituted aryls remains difficult due to steric demands. Wallace (2006) reviews early biaryl syntheses highlighting ligand limitations. Yalcouye et al. (2014) address this in steganone synthesis with atropodiastereoselective conditions.
Scalability to Natural Products
Achieving high enantioselectivity while scaling reactions for complex molecules challenges optimization. Shimamura et al. (2010) used Pd(0)-indole annulation for complestatin but noted macrocycle strain issues. Bringmann et al. (2004) employed lactone methods for biarylic alkaloids with scale limitations.
Control of Multiple Axes
Synthesizing atropisomers with multiple stereogenic axes requires precise catalyst control. Bao et al. (2020) outline difficulties in assembling dual axes via coupling. Carmona et al. (2021) classify strategies but note gaps in dynamic kinetic resolutions for multi-axis systems.
Essential Papers
Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies
José A. Carmona, Carlos Rodríguez-Franco, Rosario Fernández et al. · 2021 · Chemical Society Reviews · 379 citations
Atroposelective transformations of (hetero)biaryls are classified into desymmetrization, kinetic resolution, dynamic kinetic resolution, and dynamic kinetic asymmetric transformation depending on t...
Enantioselective Synthesis of Atropisomers with Multiple Stereogenic Axes
Xiaoze Bao, Jean Rodriguez, Damien Bonne · 2020 · Angewandte Chemie International Edition · 186 citations
Abstract Atropisomers possessing multiple stereogenic axes are intriguing molecules with huge potential. However, only few approaches for their enantioselective synthesis are available due to the d...
Organocatalytic atroposelective synthesis of axially chiral styrenes
Sheng‐Cai Zheng, San Wu, Qinghai Zhou et al. · 2017 · Nature Communications · 177 citations
Abstract Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of...
Biaryl synthesis with control of axial chirality
Timothy W. Wallace · 2006 · Organic & Biomolecular Chemistry · 165 citations
Biaryls have been a persistent focus of interest for chemists since it was recognised, more than 80 years ago, that they can manifest the axial chirality that is inherent in structures consisting o...
A Bird's Eye View of Atropisomers Featuring a Five‐Membered Ring
Damien Bonne, Jean Rodriguez · 2018 · European Journal of Organic Chemistry · 159 citations
An atropisomer is a member of a subclass of restricted rotational conformers – this restricted rotation giving rise to stereogenic sigma bonds – that can be isolated as separate chemical species. M...
Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction
Jiwei Zhang, Jinhui Xu, Dao‐Juan Cheng et al. · 2016 · Nature Communications · 147 citations
Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
Changgui Zhao, Donghui Guo, Kristin Munkerup et al. · 2018 · Nature Communications · 139 citations
Abstract Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for th...
Reading Guide
Foundational Papers
Start with Wallace (2006) for biaryl chirality overview (165 citations), then Yalcouye et al. (2014) for atropodiastereoselective Suzuki in steganone synthesis, and Bringmann et al. (2004) for lactone ligand applications.
Recent Advances
Study Carmona et al. (2021, 379 citations) for atroposelective classifications and Bao et al. (2020, 186 citations) for multi-axis synthesis advances.
Core Methods
Core techniques: chiral phosphine/Pd catalysts (Shimamura et al., 2010), atropodiastereoselective biaryl coupling (Yalcouye et al., 2014), and dynamic kinetic resolutions (Carmona et al., 2021).
How PapersFlow Helps You Research Atroposelective Suzuki-Miyaura Coupling
Discover & Search
Research Agent uses searchPapers and citationGraph on 'atroposelective Suzuki-Miyaura' to map 165-citation Wallace (2006) as hub, linking to Yalcouye et al. (2014) and Shimamura et al. (2010); exaSearch uncovers niche ligand designs, while findSimilarPapers expands to 50+ related biaryl syntheses.
Analyze & Verify
Analysis Agent applies readPaperContent to extract conditions from Yalcouye et al. (2014), verifies enantioselectivity claims with verifyResponse (CoVe) against Carmona et al. (2021), and uses runPythonAnalysis for plotting yield-enantiomeric excess correlations from tabulated data; GRADE grading scores evidence strength for ligand efficacy.
Synthesize & Write
Synthesis Agent detects gaps in multi-axis control from Bao et al. (2020) vs. Wallace (2006); Writing Agent employs latexEditText for reaction schemes, latexSyncCitations to integrate 10+ references, and latexCompile for polished reviews; exportMermaid visualizes coupling mechanism flows.
Use Cases
"Extract reaction conditions from atroposelective Suzuki papers and plot ee vs yield in Python."
Research Agent → searchPapers('atroposelective Suzuki-Miyaura') → Analysis Agent → readPaperContent(Yalcouye 2014) + runPythonAnalysis(pandas plot ee-yield scatter) → matplotlib graph of 20+ conditions.
"Write LaTeX review of Suzuki ligands for axial chirality with citations."
Synthesis Agent → gap detection(Wallace 2006, Carmona 2021) → Writing Agent → latexEditText(draft) → latexSyncCitations(10 papers) → latexCompile → PDF with biaryl schemes.
"Find GitHub repos with code for atroposelective coupling simulations."
Research Agent → paperExtractUrls(Shimamura 2010) → Code Discovery → paperFindGithubRepo → githubRepoInspect → curated list of DFT optimization scripts for Pd catalysts.
Automated Workflows
Deep Research workflow scans 50+ papers via citationGraph from Wallace (2006), generating structured reports on ligand evolution with GRADE scores. DeepScan applies 7-step CoVe to verify Yalcouye et al. (2014) conditions against Bringmann et al. (2004). Theorizer hypothesizes new phosphine ligands from patterns in Carmona et al. (2021) and Bao et al. (2020).
Frequently Asked Questions
What defines atroposelective Suzuki-Miyaura coupling?
It uses chiral catalysts for enantioselective biaryl formation via aryl boronic acid-halide coupling, targeting axial chirality (Wallace, 2006).
What are main methods in this subtopic?
Methods include atropodiastereoselective Suzuki with lactone auxiliaries (Yalcouye et al., 2014) and Pd(0)-mediated annulations (Shimamura et al., 2010).
What are key papers?
Wallace (2006, 165 citations) reviews biaryl chirality control; Yalcouye et al. (2014) demonstrates steganone synthesis; Carmona et al. (2021, 379 citations) classifies atroposelective strategies.
What open problems exist?
Challenges include multi-axis control (Bao et al., 2020) and scalable enantioselective couplings for highly hindered biaryls beyond natural products.
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