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PreprintCC BY-NC-NDChemRxiv

Synthesis of 5-Aminoisoxazolidines from Azetidine Nitrones via Formal Ring Expansion

  • Dylan C. Keane1
  • Abdullah S. Alshreimi1
  • Laura Alonso1
  • Oishik Sarkar1
  • Lam Minh Uyen Phan1
  • Benjamin Stageberg1
  • Donald J. Wink1
  • Laura L. Anderson1
  1. 1Department of Chemistry, University of Illinois Chicago, 845 W. Taylor St., MC 111, Chicago, IL, USA, 60607
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Abstract

A formal ring-expansion reaction of azetidine nitrones has been developed for the synthesis of 5-aminoisoxazolidines. Nucleophilic addition of an amine, alcohol or water to an azetidine nitrone is proposed to initiate azetidine nitrone ring-opening followed by cyclization to the corresponding 5-membered ring. A variety of examples are presented highlighting the scope of the method as well as the differences in stereochemical preference between primary aniline and secondary amine nucleophiles. A two-step, one-pot process is also described for the direct conversion of N-alkenylnitrones to 5-aminoisoxazolidines.

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Cite

BibTeXRIS
BibTeX
@misc{keane2026synthesis,
  title = {{Synthesis of 5-Aminoisoxazolidines from Azetidine Nitrones via Formal Ring Expansion}},
  author = {Dylan C. Keane and Abdullah S. Alshreimi and Laura Alonso and Oishik Sarkar and Lam Minh Uyen Phan and Benjamin Stageberg and Donald J. Wink and Laura L. Anderson},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15007888/v2},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007888/v2},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Synthesis of 5-Aminoisoxazolidines from Azetidine Nitrones via Formal Ring Expansion
AU  - Dylan C. Keane
AU  - Abdullah S. Alshreimi
AU  - Laura Alonso
AU  - Oishik Sarkar
AU  - Lam Minh Uyen Phan
AU  - Benjamin Stageberg
AU  - Donald J. Wink
AU  - Laura L. Anderson
PY  - 2026
DA  - 2026/09/17
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15007888/v2
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007888/v2
AB  - A formal ring-expansion reaction of azetidine nitrones has been developed for the synthesis of 5-aminoisoxazolidines. Nucleophilic addition of an amine, alcohol or water to an azetidine nitrone is proposed to initiate azetidine nitrone ring-opening followed by cyclization to the corresponding 5-membered ring. A variety of examples are presented highlighting the scope of the method as well as the differences in stereochemical preference between primary aniline and secondary amine nucleophiles. A two-step, one-pot process is also described for the direct conversion of N-alkenylnitrones to 5-aminoisoxazolidines.
ER  -