Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess
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Asymmetric amplification during self‐replication is a key feature that is used to explain the origin of homochirality. Asymmetric autocatalysis of pyrimidyl alkanol in the asymmetric addition of diisopropylzinc to pyrimidine‐5‐carbaldehyde is a unique example of this phenomenon. Crystallization of zinc alkoxides of this 5‐pyrimidyl alkanol and single‐crystal X‐ray diffraction analysis of the alkoxide crystals reveal the existence of tetramer or higher oligomer structures in this asymmetric autocatalytic system.
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The crystal structures of asymmetric autocatalysts 1c are either tetrameric or oligomeric, as determined by X-ray diffraction.
“We found that the crystal structures of asymmetric autocatalysts 1c are either tetrameric or oligomeric, as determined by X-ray diffraction (Fig. 3).66,67)”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [66]
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- Authors
- Matsumoto, A., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K.
- Affiliations
- Tokyo University of Science (JP)
- University of Fukui (JP)
- Corresponding author
- Matsumoto, Arimasa
- Kawasaki, Tsuneomi
- Soai, Kenso
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2015-10-23
- Volume
- 54
- Issue
- 50
- Pages
- 15218-15221
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- PMC
- PMC4691336
- OpenAlex
- W2112684268
- Cited by
- 75
- References
- 112
- Citations by year
- 2026: 2 · 2025: 4 · 2024: 2 · 2023: 3 · 2022: 12 · 2021: 5 · 2020: 7 · 2019: 10 · 2018: 5 · 2017: 14 · 2016: 11
- FWCI
- 4.58
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed Central (publishedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- Funders
- Funded Access
- Grant-in-Aid for Scientific Research
- Japan Society for the Promotion of Science
- JSPS (23685012, 26810026, 15H03781)
- MEXT
- 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
- asymmetric autocatalysis, origin of homochirality, pyrimidine-5-carbaldehyde, oligomeric structure, tetramer, crystal structure, enantioselective addition
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