Evidence of Asymmetric Autocatalysis in Organocatalytic Reactions
Open accessAbstract
When product and catalyst are the same: The chiral product 3 of an asymmetric Mannich reaction (see scheme), investigated under various experimental conditions and by calculations, is shown to act as a chiral catalyst for its own formation (autocatalysis). A generally applicable catalytic cycle is proposed to involve equilibria between hydrogen-bonded substrate–product complexes.
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Reports by Tsogoeva of a purely organic reaction showing similar properties of autocatalysis and amplification of ee have excited the community, because the chemistry involved is much closer to what could be prebiotically plausible.
“Most recently, reports by Tsogoeva (Mauksch et al. 2007) of a purely organic reaction showing similar properties of autocatalysis and amplification of ee (Scheme 3) have excited the community, because the chemistry involved is much closer to what could be prebiotically plausible.”
From The Origin of Biological Homochirality (2010) · cites this paper as Mauksch et al. 2007
In the main text (pp. 393–396), Mauksch et al. report a purely organic Mannich reaction in which the chiral product can catalyze its own formation. The reported product ee values are generally similar to or lower than the starting catalyst ee, so the paper does not establish amplification of ee. Our copy also does not assess prebiotic plausibility. (LLM, conf=0.88)
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Mauksch, M. (2022) · Physical Chemistry Chemical Physics · doi:10.1039/d2cp04285a · Cited by 10 · see citing works
Self-citationChelation-Controlled Additions to α-Silyloxy Aldehydes: An Autocatalytic Approach
Raffier, L., Stanton, G. R., & Walsh, P. J. (2013) · Organic Letters · doi:10.1021/ol4030259 · Cited by 9 · see citing works
Speeding up Viedma Deracemization through Water‐catalyzed and Reactant Self‐catalyzed Racemization
Tortora, C., Mai, C., Cascella, F., Mauksch, M., Seidel‐Morgenstern, A., Lorenz, H., & Tsogoeva, S. B. (2020) · ChemPhysChem · doi:10.1002/cphc.202000493 · Cited by 8 · see citing works
Self-citationKano, T., Maruyama, H., Akiyama, K., & Maruoka, K. (2014) · Tetrahedron Letters · doi:10.1016/j.tetlet.2014.05.049 · Cited by 8 · see citing works
Spontaneous Emergence of Transient Chirality in Closed, Reversible Frank-like Deterministic Models
Buhse, T., & Micheau, J. C. (2022) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-022-09621-y · Cited by 6 · see citing works
“There is also the Mannich reaction for which has been shown that the product can be a promising catalyst for its own formation (Mauksch et al. 2007; Amedjkouh and Brandberg 2008).”
BackgroundLife's Single Chirality: Origin of Symmetry Breaking in Biomolecules
Mauksch, M., & Tsogoeva, S. B. (2011) · Wiley eBooks · doi:10.1002/9783527634606.ch23 · Cited by 7 · see citing works
Self-citationSearching for Spontaneous Mirror-Symmetry Breaking in Organoautocatalytic Reactions
Valero, G., & Moyano, A. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00013-7 · Cited by 6 · see citing works
Organocatalytic Mannich type reactions of glyoxylate imines and related compounds
Šramel, P., & Šebesta, R. (2024) · Tetrahedron Letters · doi:10.1016/j.tetlet.2024.155129 · Cited by 4 · see citing works
Spontaneous Elliptical Polarization of Racemic Multilayer Polymers and Oligomers
Zhang, S., Yuan, Q., Wang, Y., Tang, Y., Rahman, A. U., Jin, S., Wang, J., Xu, T. S., & Li, G. (2025) · ChemistrySelect · doi:10.1002/slct.202501960 · Cited by 5 · see citing works
Kinetic and Structural Aspects of Mirror-Image Symmetry Breaking in the Soai Reaction
Buhse, T., Noble‐Terán, M. E., Cruz, J., Micheau, J. C., & Coudret, C. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00004-6 · Cited by 4 · see citing works
Chemical Models for the Origin of Biological Homochirality
Klußmann, M. (2012) · Cellular origin and life in extreme habitats · doi:10.1007/978-94-007-2941-4_26 · Cited by 3 · see citing works
Development of an Organoautocatalyzed Double σ‐Bond C(sp 2 )‐N Transamination Metathesis Reaction
Klein, V., Schuster, F., Amthor, J., Maid, H., Bijalwan, P., Himo, F., Santoro, S., & Tsogoeva, S. B. (2025) · Angewandte Chemie International Edition · doi:10.1002/anie.202505275 · Cited by 2 · see citing works
Self-citationDevelopment of an Organoautocatalyzed Double σ‐Bond C(sp 2 )‐N Transamination Metathesis Reaction
Klein, V., Schuster, F., Amthor, J., Maid, H., Bijalwan, P., Himo, F., Santoro, S., & Tsogoeva, S. B. (2025) · Angewandte Chemie · doi:10.1002/ange.202505275 · Cited by 2 · see citing works
Self-citationAutocatalysis and organocatalysis with Kemp's triacid compounds
Rebek, J., Kamioka, S., Ajami, D., Sather, A. C., & Hooley, R. (2010) · Heterocycles · doi:10.3987/com-10-s(e)31 · Cited by 2 · see citing works
Connections Between Mathematical Models of Prebiotic Evolution and Homochirality
Blanco, C., & Chen, I. A. (2018) · Nucleic acids and molecular biology · doi:10.1007/978-3-319-93584-3_9 · Cited by 2 · see citing works
Examples of Metal‐Free Direct Catalytic Asymmetric Mannich‐Type Reactions Using Aminocatalysis
Córdova, A. (2013) · doi:10.1002/9781118604755.ch04 · Cited by 2 · see citing works
Rare, Neglected and Potential Synthetic Methods for the Separation of Enantiomers
Todd, M. H. (2014) · Wiley eBooks · doi:10.1002/9783527650880.ch7
Amedjkouh, M., & Brandberg, M. (2008) · Chemical Communications · doi:10.1039/b716110g
RetractedReactions of Aldehydes and Ketones and their Derivatives
Knipe, A. C. (2007) · Organic Reaction Mechanisms/Organic reaction mechanisms · doi:10.1002/9780470975800.ch1
- Authors
- Mauksch, M., Tsogoeva, S. B., Martynova, I. M., & Wei, S.
- Affiliations
- University of Göttingen (DE)
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2006-12-27
- Volume
- 46
- Issue
- 3
- Pages
- 393-396
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2104976075
- Cited by
- 103
- References
- 19
- Citations by year
- 2026: 1 · 2025: 5 · 2024: 1 · 2023: 1 · 2022: 3 · 2021: 2 · 2020: 3 · 2019: 2 · 2018: 4 · 2017: 5 · 2016: 3 · 2015: 2 · 2014: 5 · 2013: 6 · 2012: 3
- FWCI
- 7.21
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- GRO (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Physical Sciences › Chemistry › Inorganic Chemistry › Asymmetric Hydrogenation and Catalysis
- Keywords
- asymmetric autocatalysis, organocatalysis, asymmetric Mannich reaction, chiral catalysts, catalytic cycle
- MeSH terms
- Catalysis, Models, Molecular, Organic Chemicals, Proline, Stereoisomerism, Molecular Structure
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