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PreprintCC BYChemRxiv

Computational Analysis of Competing Reduction Pathways in the Asymmetric Transfer Hydrogenation of 2-Alkenylquinolines

  • Adrián López-Francés1
  • Aitor Maestro2,3
  1. 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom, OX1 3TA
  2. 2Department of Chemistry, Faculty of Science and Engineering
  3. 3Swansea University
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Abstract

Two competing reduction pathways can deliver a single stereochemical outcome. This computational study reveals that asymmetric transfer hydrogenation of 2-alkenylquinolines can begin through nearly isoenergetic 1,4-hydride transfer to either the quinoline ring or the alkenyl side chain. The resulting sequences converge on a common prochiral iminium intermediate, after which a final chiral phosphoric acid-controlled 1,2-hydride transfer establishes the experimentally observed enantioselectivity, providing a rational explanation of how competing reduction sequences ultimately afford the same product and stereochemical outcome.

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Cite

BibTeXRIS
BibTeX
@misc{lopezfrances2026computational,
  title = {{Computational Analysis of Competing Reduction Pathways in the Asymmetric Transfer Hydrogenation of 2-Alkenylquinolines}},
  author = {Adrián López-Francés and Aitor Maestro},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15009686/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009686/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Computational Analysis of Competing Reduction Pathways in the Asymmetric Transfer Hydrogenation of 2-Alkenylquinolines
AU  - Adrián López-Francés
AU  - Aitor Maestro
PY  - 2026
DA  - 2026/09/30
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009686/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009686/v1
AB  - Two competing reduction pathways can deliver a single stereochemical outcome. This computational study reveals that asymmetric transfer hydrogenation of 2-alkenylquinolines can begin through nearly isoenergetic 1,4-hydride transfer to either the quinoline ring or the alkenyl side chain. The resulting sequences converge on a common prochiral iminium intermediate, after which a final chiral phosphoric acid-controlled 1,2-hydride transfer establishes the experimentally observed enantioselectivity, providing a rational explanation of how competing reduction sequences ultimately afford the same product and stereochemical outcome.
ER  -