Cited by 37Origins and Evolution of LifeAsymmetric Synthesis and CatalysisChemistry and Stereochemistry Studies

Asymmetric Strecker Reaction Arising from the Molecular Orientation of an Achiral Imine at the Single‐Crystal Face: Enantioenriched l‐ and d‐Amino Acids

Miyagawa, Shinobu, Yoshimura, Koji, Yamazaki, Yusuke, Takamatsu, Naoya, Kuraishi, Tetsuya, Aiba, Shohei, Tokunaga, Yuji, Kawasaki, Tsuneomi·2017·Angewandte Chemie International Edition

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.

Integrity signals

Registry

Crossref · 10.1002/anie.201611128

Cites

52 of 52 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

We couldn’t retrieve this paper’s full text, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • 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”

Cites

Flagged first, then by citations

Cited by

Sorted by citations

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

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review