Absolute Autocatalytic Amplification under Heterogenous Phase Conditions Involving Subsequent Hydride Transfer and a Hemiacetal Intermediate
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Abstract
Abstract : In contrast to the homogenous phase, absolute asymmetric amplification of pyridine alkanol is observed under heterogenous conditions. The reaction of iPr 2 Zn vapor on a solid powder of pyridine carbaldehyde induced autocatalytic amplification of chirality providing the alkanol product with an enantiopurity up to 90 % ee. In this study, side products were identified and their formation is traced back to redox pathways involving hydride transfer, namely a chiral ester resulting most probably from a disproportionation of the starting aldehyde into a hemiacetal and subsequent hydride loss following a Claisen‐Tishchenko mechanism. These observations provide new perspectives in the elucidation of the mechanism of amplification of chirality in the Soai reaction.
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The outcome of the Soai reaction in absence of detectable chiral species is stochastic.
“In addition, the apparent outcome of the Soai reaction performed in the absence of detectable chiral species is stochastic as expected for a truly SMSB process”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [333]
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References 52 · Cited by 12
- Authors
- Rotunno, G., Petersen, D., & Amedjkouh, M.
- Affiliations
- University of Oslo (NO)
- Corresponding author
- Amedjkouh, Mohamed
- ORCID
- Amedjkouh, Mohamed
- Venue
- ChemSystemsChem
- Publisher
- Wiley
- Published
- 2020-02-05
- Volume
- 2
- Issue
- 5
- ISSN
- 2570-4206 (ISSN-L)
- OpenAlex
- W3004925664
- Cited by
- 12
- References
- 52
- Citations by year
- 2025: 1 · 2023: 1 · 2022: 5 · 2021: 2 · 2020: 3
- FWCI
- 1.07
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- ChemSystemsChem (publishedVersion, other-oa)
- ChemRxiv (acceptedVersion, cc-by-nc-nd)
- Figshare (submittedVersion, cc-by-nc-nd)
- NORA - Norwegian Open Research Archives (submittedVersion, other-oa)
- Funders
- Norges Forskningsråd (250795)
- Universitetet i Oslo
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- Soai reaction, heterogeneous catalysis, hydride transfer, hemiacetal intermediate, enantiomeric purity, redox pathways
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