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Asymmetric Hydrogenation and Catalysis
Research Guide
What is Asymmetric Hydrogenation and Catalysis?
Asymmetric hydrogenation and catalysis refers to homogeneous catalysis using transition metal complexes with chiral ligands to achieve enantioselective hydrogenation reactions that produce single enantiomers of chiral molecules.
This field encompasses 74,983 papers on advances in asymmetric catalysis, hydrogenation, chiral ligands, and enantioselective reactions with transition metals. Key aspects include alcohol activation, dehydrogenation, amine synthesis, borrowing hydrogen, and metal-ligand cooperation. Foundational work established steric effects of phosphorus ligands in these processes, as detailed in Tolman (1977).
Topic Hierarchy
Research Sub-Topics
Asymmetric Hydrogenation Catalysts
This sub-topic studies transition metal catalysts and chiral ligands for enantioselective hydrogenation of alkenes, ketones, and imines. Researchers optimize activity, selectivity, and substrate scope using Rh, Ru, and Ir complexes.
Chiral Ligand Design
This sub-topic focuses on the synthesis, steric/electronic tuning, and structure-activity relationships of phosphine, N-heterocyclic, and hybrid chiral ligands. Researchers employ computational modeling and high-throughput screening for optimization.
Borrowing Hydrogen Catalysis
This sub-topic examines metal-catalyzed dehydrogenation of alcohols followed by nucleophilic addition and hydrogenation for C-N and C-C bond formation. Researchers investigate mechanisms and scope for amine and alkylated product synthesis.
Enantioselective Alcohol Activation
This sub-topic covers catalytic activation of alcohols for asymmetric substitution, coupling, and dehydrogenation reactions. Researchers develop cooperative metal-ligand systems for high enantiocontrol.
Metal-Ligand Cooperation Catalysis
This sub-topic explores bifunctional catalysis where both metal and ligand centers participate in substrate activation and bond breaking. Researchers study pincer complexes and non-innocent ligands for dehydrogenation and transfer reactions.
Why It Matters
Asymmetric hydrogenation and catalysis enables production of enantiomerically pure compounds essential for pharmaceuticals and fine chemicals. Trost and Van Vranken (1996) demonstrated asymmetric transition metal-catalyzed allylic alkylations achieving high enantioselectivity for complex molecule synthesis. Jacobsen et al. (1999) provided comprehensive methods for asymmetric catalysis, including hydrogenation, applied in industrial-scale production of drugs like (S)-naproxen. These techniques improve atom economy, as Trost (1991) quantified with metrics showing maximum reactant atoms incorporated into products, reducing waste in large-scale manufacturing.
Reading Guide
Where to Start
"Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis" (Tolman, 1977) provides foundational understanding of ligand effects critical to asymmetric catalysis design.
Key Papers Explained
Tolman (1977) established steric parameters for phosphorus ligands used in hydrogenation. Trost (1991) connected these to atom-efficient asymmetric synthesis principles. "Comprehensive asymmetric catalysis" (Jacobsen et al., 1999) integrates them into practical enantioselective methods, while Trost and Van Vranken (1996) apply to allylic alkylations building on palladium catalysis from Beletskaya and Cheprakov (2000).
Paper Timeline
Most-cited paper highlighted in red. Papers ordered chronologically.
Advanced Directions
Research continues on transition metal complexes for enantioselective reactions, borrowing hydrogen, and metal-ligand cooperation, as reflected in the 74,983 papers without recent preprints noted.
Papers at a Glance
| # | Paper | Year | Venue | Citations | Open Access |
|---|---|---|---|---|---|
| 1 | Steric effects of phosphorus ligands in organometallic chemist... | 1977 | Chemical Reviews | 4.7K | ✕ |
| 2 | The Atom Economy—A Search for Synthetic Efficiency | 1991 | Science | 4.7K | ✕ |
| 3 | Palladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reacti... | 2009 | Angewandte Chemie Inte... | 4.1K | ✓ |
| 4 | The Heck Reaction as a Sharpening Stone of Palladium Catalysis | 2000 | Chemical Reviews | 3.8K | ✕ |
| 5 | Catalytic Dehydrogenative Cross-Coupling: Forming Carbon−Carbo... | 2011 | Chemical Reviews | 3.8K | ✕ |
| 6 | Comprehensive asymmetric catalysis | 1999 | Springer eBooks | 3.8K | ✕ |
| 7 | Catalytic Asymmetric Dihydroxylation | 1994 | Chemical Reviews | 3.7K | ✕ |
| 8 | Controlled Microwave Heating in Modern Organic Synthesis | 2004 | Angewandte Chemie Inte... | 3.5K | ✕ |
| 9 | Gold Catalysis | 2006 | Angewandte Chemie Inte... | 3.4K | ✕ |
| 10 | Asymmetric Transition Metal-Catalyzed Allylic Alkylations | 1996 | Chemical Reviews | 3.1K | ✕ |
Frequently Asked Questions
What role do chiral ligands play in asymmetric hydrogenation?
Chiral ligands direct transition metal complexes to produce enantioselective hydrogenation outcomes. Tolman (1977) analyzed steric effects of phosphorus ligands, showing how cone angles influence reactivity and selectivity in organometallic catalysis. These ligands enable metal-ligand cooperation for reactions like borrowing hydrogen.
How does asymmetric catalysis achieve enantioselectivity?
Asymmetric catalysis uses chiral environments around metal centers to favor one enantiomer. "Comprehensive asymmetric catalysis" (Jacobsen et al., 1999) covers methods for enantioselective hydrogenation and related transformations. Trost and Van Vranken (1996) showed allylic alkylations with up to 99% ee using palladium catalysts.
What are key methods in asymmetric hydrogenation?
Methods include transition metal-catalyzed reductions with chiral ligands for alkenes and ketones. "Asymmetric Transition Metal-Catalyzed Allylic Alkylations" (Trost and Van Vranken, 1996) details palladium systems for C-C bond formation with high enantiocontrol. These build on foundational steric parameter studies by Tolman (1977).
What applications arise from asymmetric catalysis research?
Applications span amine synthesis, dehydrogenation, and cross-coupling via hydrogenation strategies. Trost (1991) emphasized atom economy in selective reactions for efficient synthesis. Yeung and Dong (2011) reviewed dehydrogenative cross-coupling, oxidizing C-H bonds to form C-C bonds without external oxidants.
What is the current state of asymmetric hydrogenation catalysts?
The field features 74,983 works on transition metal complexes and chiral ligands. Highly cited reviews like Tolman (1977) remain central, with 4723 citations on phosphorus ligand effects. Comprehensive texts such as Jacobsen et al. (1999) summarize established enantioselective protocols.
Open Research Questions
- ? How can chiral ligands be optimized beyond phosphorus-based systems for broader substrate scope in asymmetric hydrogenation?
- ? What mechanisms enable metal-ligand cooperation in borrowing hydrogen for amine synthesis without exogenous hydrogen?
- ? Which transition metals provide highest activity and selectivity for challenging alkene hydrogenations?
- ? How do steric effects quantified by Tolman cone angles predict outcomes in modern enantioselective catalysts?
- ? What improvements in atom economy can integrate asymmetric hydrogenation with C-H activation strategies?
Recent Trends
The field maintains 74,983 works with sustained focus on asymmetric catalysis and hydrogenation, anchored by classics like Tolman with 4723 citations and Trost (1991) with 4679 citations.
1977No new preprints or news in the last 12 months indicate steady incorporation of established methods into broader catalysis.
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