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PreprintCC BYChemRxiv

Sm-Catalyzed Reductive Transformations of Enones

  • Nathan C. Friede1,2
  • Kristen E. Gardner1,2
  • Nhu H. Quach3,4
  • Matthew Neurock3,4
  • Sarah E. Reisman1,2
4 affiliations
  1. 1Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering
  2. 2California Institute of Technology
  3. 3Department of Chemistry
  4. 4University of Minnesota
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Abstract

We report two Sm-catalyzed reductive transformations of enones. Using catalytic Sm(OTf)3 and Zn0 as the terminal reductant, Wieland–Miescher-type ketones underwent ring contraction to trans-hydrindanes bearing vicinal quaternary stereogenic centers. Under similar conditions but with 2-naphthalenethiol as a hydrogen atom donor, diastereoselective enone reduction outcompeted the ring contraction pathway, furnishing decalin products. The diastereoselectivity of the enone reduction was shown to be controlled primarily by the substrate structure; however, for certain substrates, the thiol structure could be used to improve the diastereoselectivity. Mechanistic investigation by cyclic voltammetry is also reported.

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Cite

BibTeXRIS
BibTeX
@misc{friede2026smcatalyzed,
  title = {{Sm-Catalyzed Reductive Transformations of Enones}},
  author = {Nathan C. Friede and Kristen E. Gardner and Nhu H. Quach and Matthew Neurock and Sarah E. Reisman},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010939/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010939/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Sm-Catalyzed Reductive Transformations of Enones
AU  - Nathan C. Friede
AU  - Kristen E. Gardner
AU  - Nhu H. Quach
AU  - Matthew Neurock
AU  - Sarah E. Reisman
PY  - 2026
DA  - 2026/10/23
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010939/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010939/v1
AB  - We report two Sm-catalyzed reductive transformations of enones. Using catalytic Sm(OTf)3 and Zn0 as the terminal reductant, Wieland–Miescher-type ketones underwent ring contraction to trans-hydrindanes bearing vicinal quaternary stereogenic centers. Under similar conditions but with 2-naphthalenethiol as a hydrogen atom donor, diastereoselective enone reduction outcompeted the ring contraction pathway, furnishing decalin products. The diastereoselectivity of the enone reduction was shown to be controlled primarily by the substrate structure; however, for certain substrates, the thiol structure could be used to improve the diastereoselectivity. Mechanistic investigation by cyclic voltammetry is also reported.
ER  -