Dynamic Nonlinear Effects in Asymmetric Catalysis
Abstract
For three decades, “conventional” nonlinear effects in asymmetric catalysis, commonly becoming apparent as a nonproportional relationship between the enantiomeric purity of the chiral catalyst and that of the chiral reaction product, have been extensively studied from both fundamental and practical perspectives and thoroughly reviewed. In contrast, this review is focused on dynamic nonlinear effects, with the catalyst systems exhibiting variation of enantioselectivity over the reaction course, caused by catalyst–product or catalyst–substrate interactions. Namely, such phenomena as asymmetric autoinduction, asymmetric autocatalysis, and asymmetric autoamplification are considered and the corresponding catalytic reactions are surveyed. Whenever available, data on the origins of the observed nonlinearities are presented. Several kinetic schemes, illustrating the nonlinear ee variation over the reaction course, are considered. Possible implications of dynamic nonlinear effects in asymmetric catalysis in the problem of biological homochirality on Earth are discussed briefly.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Some mechanisms are known for increasing an existing enantiomeric excess, such as self-disproportionation of enantiomers, non-linear effects in asymmetric catalysis, and stereoselective polymerization.
“Some mechanisms are known for increasing an existing e.e., such as the self-disproportionation of enantiomers (SDE), 61 non-linear effects in asymmetric catalysis, 62,63 and stereoselective polymerization.64”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [63]
Cites
Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085 · see citing works
Prebiotic Systems Chemistry: New Perspectives for the Origins of Life
Ruiz-Mirazo, K., Briones, C., & de la Escosura, A. (2014) · Chemical Reviews · doi:10.1021/cr2004844 · Cited by 930 · see citing works
Nonlinear Effects in Asymmetric Catalysis
Satyanarayana, T., Abraham, S., & Kagan, H. B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200705241 · Cited by 591 · see citing works
The Origin of Biological Homochirality
Blackmond, D. G. (2010) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a002147 · Cited by 408 · see citing works
Crystalline Architectures as Templates of Relevance to the Origins of Homochirality
Weissbuch, I., & Lahav, M. (2011) · Chemical Reviews · doi:10.1021/cr1002479 · Cited by 284 · see citing works
Soai, K., Sato, I., Shibata, T., Komiya, S., Hayashi, M., Matsueda, Y., Imamura, H., Hayase, T., Morioka, H., Tabira, H., et al. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(02)00791-7 · Cited by 266 · see citing works
The Chemistry of Life's Origin: A Carbonaceous Meteorite Perspective
Pizzarello, S. (2006) · Accounts of Chemical Research · doi:10.1021/ar050049f · Cited by 253 · see citing works
Sato, I., Urabe, H., Ishiguro, S., Shibata, T., & Soai, K. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200390105 · Cited by 232 · see citing works
Soai, K., Niwa, S., & Hori, H. (1990) · Journal of the Chemical Society, Chemical Communications · doi:10.1039/c39900000982 · Cited by 146 · see citing works
Sato, I., Omiya, D., Igarashi, H., Kato, K., Ogi, Y., Tsukiyama, K., & Soai, K. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(03)00164-2 · Cited by 138 · see citing works
Kawasaki, T., Suzuki, K., Shimizu, M., Ishikawa, K., & Soai, K. (2006) · Chirality · doi:10.1002/chir.20273 · Cited by 109 · see citing works
Evidence of Asymmetric Autocatalysis in Organocatalytic Reactions
Mauksch, M., Tsogoeva, S. B., Martynova, I. M., & Wei, S. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200603517 · Cited by 103 · see citing works
Schiaffino, L., & Ercolani, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802450 · Cited by 100 · see citing works
Gehring, T., Quaranta, M., Odell, B., Blackmond, D. G., & Brown, J. M. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203398 · Cited by 99 · see citing works
Quaranta, M., Gehring, T., Odell, B., Brown, J. M., & Blackmond, D. G. (2010) · Journal of the American Chemical Society · doi:10.1021/ja103204w · Cited by 99 · see citing works
Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions
Mauksch, M., Tsogoeva, S. B., Wei, S., & Martynova, I. M. (2007) · Chirality · doi:10.1002/chir.20474 · Cited by 89 · see citing works
Sato, I., Omiya, D., Tsukiyama, K., Ogi, Y., & Soai, K. (2001) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(01)00351-2 · Cited by 81 · see citing works
Micheau, J.-C., Coudret, C., Cruz, J.-M., & Buhse, T. (2012) · Physical Chemistry Chemical Physics · doi:10.1039/c2cp42041d · Cited by 62 · see citing works
Amedjkouh, M., & Brandberg, M. (2008) · Chemical Communications · doi:10.1039/b804142n · Cited by 54 · see citing works
Suzuki, K., Hatase, K., Nishiyama, D., Kawasaki, T., & Soai, K. (2010) · Journal of Systems Chemistry · doi:10.1186/1759-2208-1-5 · Cited by 46 · see citing works
Kinetic Insight into Specific Features of the Autocatalytic Soai Reaction
Lavabre, D., Micheau, J.-C., Islas, J. R., & Buhse, T. (2007) · Topics in Current Chemistry · doi:10.1007/128_2007_149 · Cited by 34 · see citing works
A Quantification of the Soai Reaction
Noble‐Terán, M. E., Cruz, J., Micheau, J., & Buhse, T. (2018) · ChemCatChem · doi:10.1002/cctc.201701554 · Cited by 27 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Buhse, T., Cruz, J.-M., Noble-Terán, M. E., Hochberg, D., Ribó, J. M., Crusats, J., & Micheau, J.-C. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00819 · Cited by 189 · see citing works
Possible chemical and physical scenarios towards biological homochirality
Sallembien, Q., Bouteiller, L., Crassous, J., & Raynal, M. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01179k · Cited by 186 · see citing works
- Authors
- Bryliakov, K. P.
- Affiliations
- Novosibirsk State University (RU)
- Corresponding author
- Bryliakov, Konstantin P.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-05-03
- Volume
- 9
- Issue
- 6
- Pages
- 5418-5438
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2943471335
- Cited by
- 32
- References
- 22
- Citations by year
- 2026: 3 · 2025: 6 · 2024: 3 · 2023: 6 · 2022: 5 · 2021: 5 · 2020: 3 · 2019: 1
- FWCI
- 1.37
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- ACS Catalysis (publishedVersion)
- Funders
- Russian Foundation for Basic Research (18-33-20078)
- Ministry of Science and Higher Education of Russia (AAAA-A17-117041710080-4)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Inorganic Chemistry › Asymmetric Hydrogenation and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Axial and Atropisomeric Chirality Synthesis
- Keywords
- asymmetric catalysis, asymmetric autocatalysis, enantioselectivity, catalyst-substrate interaction, enantiomeric excess, reaction kinetics
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review