Asymmetric Strecker Reaction Arising from the Molecular Orientation of an Achiral Imine at the Single‐Crystal Face: Enantioenriched l‐ and d‐Amino Acids
Abstract
Strecker synthesis has long been considered one of the prebiotic reactions for the synthesis of α‐amino acids. However, the correlation between the origin of chirality and highly enantioenriched α‐amino acids through this method remains a puzzle. In the reaction, it may be conceivable that the handedness of amino acids has been determined at the formation stage of the chiral intermediate α‐aminonitrile, that is, the enantioselective addition of hydrogen cyanide to an imine. Herein, an enantiotopic crystal surface of an achiral imine acted as an origin of chirality for the enantioselective formation of α‐aminonitriles by the addition of HCN. In conjunction with the amplification of the enantiomeric excess and multiplication of enantioenriched aminonitrile, a large amount of near enantiopure α‐amino acids, with the l‐ and d‐handedness corresponding to the molecular orientation of the imine, is reported.
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Reactions at enantiotopic surface of an organic crystal yield enantio-enriched compounds whose optical purity can be enhanced by SMSB.
“Reactions occurring at the enantiotopic surface of an organic crystal also yields enantio-enriched compounds whose optical purity can be enhanced by SMSB processes.294,295”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [295]
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- Authors
- Miyagawa, S., Yoshimura, K., Yamazaki, Y., Takamatsu, N., Kuraishi, T., Aiba, S., Tokunaga, Y., & Kawasaki, T.
- Affiliations
- University of Fukui (JP)
- Corresponding author
- Kawasaki, Tsuneomi
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2016-12-22
- Volume
- 56
- Issue
- 4
- Pages
- 1055-1058
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2567188870
- Cited by
- 37
- References
- 52
- Citations by year
- 2026: 1 · 2025: 3 · 2024: 1 · 2023: 3 · 2022: 7 · 2021: 5 · 2020: 5 · 2019: 4 · 2018: 5 · 2017: 3
- FWCI
- 1.91
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Takeda Science Foundation
- University of Fukui
- Nagase Science Technology Foundation
- Japan Society for the Promotion of Science (16K05692)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Chemistry and Stereochemistry Studies
- Keywords
- Strecker reaction, asymmetric Strecker reaction, α-amino acids, α-aminonitriles, imines, prebiotic chemistry, enantiomeric excess amplification
- MeSH terms
- Amino Acids, Crystallization, Imines, Molecular Conformation, Nitriles, Stereoisomerism
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