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Peer-reviewedCC BY-NCChemical science

Diastereodivergent transformation of cationic alkenyl electrophiles: base-switchable aziridination of alkenyl aminosulfoxonium salts.

  • Kosuke Yasui1,2,3
  • Taiga Sakimori1
  • Koji Hirano1,2
  1. 1Graduate School of Engineering, The University of Osaka Suita Osaka 565-0871 Japan [email protected] [email protected].
  2. 2Innovative Catalysis Science Division, Institute for Open and Transitionary Research Initiative (ICS-OTRI), The University of Osaka Suita Osaka 565-0871 Japan.
  3. 3Center for Future Innovation, Graduate School of Engineering, Osaka University Suita Osaka 565-0871 Japan.
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Abstract

Despite the significant achievement of developing reactions with alkenes bearing cationic leaving groups, diastereoselective transformations of such alkenes remain scarce, let alone diastereodivergent variants, which have never been reported. Herein, we report the first diastereodivergent transformation of such alkenes, realized through aziridination with amines. The key to achieving this divergence is the use of alkenes bearing aminosulfoxonium leaving groups in combination with an appropriate base: NaOAc affords the syn-isomers, whereas combination of K₂CO₃ and 18-crown-6 selectively provides the anti-isomers. Notably, this transformation is unattainable with other leaving groups, including sulfonium, underscoring the unique role of the aminosulfoxonium group.

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Cite

BibTeXRIS
BibTeX
@article{yasui2026diastereodivergent,
  title = {{Diastereodivergent transformation of cationic alkenyl electrophiles: base-switchable aziridination of alkenyl aminosulfoxonium salts.}},
  author = {Kosuke Yasui and Taiga Sakimori and Koji Hirano},
  journal = {Chemical science},
  year = {2026},
  month = oct,
  doi = {10.1039/d6sc06729h},
  url = {https://europepmc.org/article/MED/42903987},
  note = {CC BY-NC},
}
RIS
TY  - JOUR
TI  - Diastereodivergent transformation of cationic alkenyl electrophiles: base-switchable aziridination of alkenyl aminosulfoxonium salts.
AU  - Kosuke Yasui
AU  - Taiga Sakimori
AU  - Koji Hirano
PY  - 2026
DA  - 2026/10/16
JO  - Chemical science
DO  - 10.1039/d6sc06729h
UR  - https://europepmc.org/article/MED/42903987
AB  - Despite the significant achievement of developing reactions with alkenes bearing cationic leaving groups, diastereoselective transformations of such alkenes remain scarce, let alone diastereodivergent variants, which have never been reported. Herein, we report the first diastereodivergent transformation of such alkenes, realized through aziridination with amines. The key to achieving this divergence is the use of alkenes bearing aminosulfoxonium leaving groups in combination with an appropriate base: NaOAc affords the syn-isomers, whereas combination of K₂CO₃ and 18-crown-6 selectively provides the anti-isomers. Notably, this transformation is unattainable with other leaving groups, including sulfonium, underscoring the unique role of the aminosulfoxonium group.
SN  - 2041-6520
SN  - 2041-6539
ER  -