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PreprintCC BYChemRxiv

Oxalyl Halide-Mediated Synthesis of Halogenated α,β-Unsaturated γ-Lactams from Amino Acid Derivatives

  • Hajar Aledwan1,2
  • Abhijit Kashid1,2
  • Natalia Fridman3,4
  • Abed Saady1,2
4 affiliations
  1. 1Department of Chemistry
  2. 2Bar-Ilan University
  3. 3Schulich Faculty of Chemistry
  4. 4Technion-Israel Institute of Technology
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Abstract

An oxalyl halide-mediated conversion of amino acid derivatives to halogenated α,β-unsaturated γ-lactams is reported. The metal-free transformation provides functionalized γ-lactams from readily available amino acid derivatives. Variation of the amine substituent, oxalyl halide, amino acid side chain, and external nucleophile enables independent diversification at N1, C3, C4, and C5, respectively. Mechanistic studies support an activation-cyclization-halogenation sequence involving multiple modes of oxalyl halide reactivity.

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Cite

BibTeXRIS
BibTeX
@misc{aledwan2026oxalyl,
  title = {{Oxalyl Halide-Mediated Synthesis of Halogenated α,β-Unsaturated γ-Lactams from Amino Acid Derivatives}},
  author = {Hajar Aledwan and Abhijit Kashid and Natalia Fridman and Abed Saady},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15011055/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011055/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Oxalyl Halide-Mediated Synthesis of Halogenated α,β-Unsaturated γ-Lactams from Amino Acid Derivatives
AU  - Hajar Aledwan
AU  - Abhijit Kashid
AU  - Natalia Fridman
AU  - Abed Saady
PY  - 2026
DA  - 2026/10/26
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15011055/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011055/v1
AB  - An oxalyl halide-mediated conversion of amino acid derivatives to halogenated α,β-unsaturated γ-lactams is reported. The metal-free transformation provides functionalized γ-lactams from readily available amino acid derivatives. Variation of the amine substituent, oxalyl halide, amino acid side chain, and external nucleophile enables independent diversification at N1, C3, C4, and C5, respectively. Mechanistic studies support an activation-cyclization-halogenation sequence involving multiple modes of oxalyl halide reactivity.
ER  -