Cited by 76Asymmetric Synthesis and CatalysisOrigins and Evolution of LifeChemical Reaction Mechanisms

Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess

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Matsumoto, Arimasa, Abe, Takaaki, Hara, Atsushi, Tobita, Takayuki, Sasagawa, Taisuke, Kawasaki, Tsuneomi, Soai, Kenso·2015·Angewandte Chemie International Edition

Abstract

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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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
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
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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