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PreprintCC BYChemRxiv

CuBr-Catalyzed Enantioselective Synthesis of Decahydroquinoxaline-Based

  • Laxman Alakonda1,2
  • Mariappan Periasamy3,4
4 affiliations
  1. 1School of Pharmacy
  2. 2University of Wyoming
  3. 3School of Chemistry
  4. 4University of Hyderabad
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Abstract

A CuBr-catalyzed one-pot protocol provides access to decahydroquinoxaline-based bis(propargylamines) from readily available terminal alkynes, aromatic aldehydes, and a C2symmetric chiral diamine. The three-component coupling proceeds at 120 °C within 12 h, affording the products in 58–93% yields with diastereomeric ratios of up to 99:1. The synthetic utility of the protocol is illustrated by the ZnI2-mediated conversion of a representative bis(propargylamine) (7a) into the corresponding axially chiral allene (8a) with 90% ee. This approach enables the stereoselective construction of bis(propargylamines) and demonstrates their application as precursors to axially chiral allenes.

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Cite

BibTeXRIS
BibTeX
@misc{alakonda2026cubrcatalyzed,
  title = {{CuBr-Catalyzed Enantioselective Synthesis of Decahydroquinoxaline-Based}},
  author = {Laxman Alakonda and Mariappan Periasamy},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15009369/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009369/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - CuBr-Catalyzed Enantioselective Synthesis of Decahydroquinoxaline-Based
AU  - Laxman Alakonda
AU  - Mariappan Periasamy
PY  - 2026
DA  - 2026/09/23
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009369/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009369/v1
AB  - A CuBr-catalyzed one-pot protocol provides access to decahydroquinoxaline-based bis(propargylamines) from readily available terminal alkynes, aromatic aldehydes, and a C2symmetric chiral diamine. The three-component coupling proceeds at 120 °C within 12 h, affording the products in 58–93% yields with diastereomeric ratios of up to 99:1. The synthetic utility of the protocol is illustrated by the ZnI2-mediated conversion of a representative bis(propargylamine) (7a) into the corresponding axially chiral allene (8a) with 90% ee. This approach enables the stereoselective construction of bis(propargylamines) and demonstrates their application as precursors to axially chiral allenes.
ER  -