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Peer-reviewedCC BY-NCScience Advances

Optical resolution of H/D isotopic chirality via asymmetric C–H amination

  • Tatsuya Uchida1,2,3,4
  • Yuta Nakagawa1
  • Naoki Watari1
  • Yuuya Kawasaki5
5 affiliations
  1. 1Department of Chemistry, Graduate School of Sciences, Kyushu University; Fukuoka, 819-0395, Japan.
  2. 2International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University; Fukuoka, 819-0395, Japan.
  3. 3Faculty of Arts and Science, Kyushu University; Fukuoka, 819-0395, Japan.
  4. 4JST PRESTO; Tokyo, 102-0076, Japan.
  5. 5Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580, Japan.
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Abstract

Isotopic chirality arising from hydrogen/deuterium substitution has long resisted optical resolution because isotopic substitution introduces only minimal stereochemical differences, rendering such molecules structurally pseudo-achiral. Recognizing that the small yet distinct difference in C–H/C–D bond dissociation energies (BDEs) creates an energetic asymmetry, we envisioned that an enantioselective C–H functionalization exploiting this disparity could achieve the kinetic resolution of isotopically chiral molecules. Here, we report a catalytic method for the optical resolution of benzylic and allylic H/D isotopic chirality. This method achieved a remarkably high separation factor ( S = 83.1), enabling the isolation of highly enantioenriched isotopically chiral substrates from racemic mixtures and revealing retention of stereochemical memory during radical recombination in asymmetric C–H functionalization.

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Cite

BibTeXRIS
BibTeX
@article{uchida2026optical,
  title = {{Optical resolution of H/D isotopic chirality via asymmetric C–H amination}},
  author = {Tatsuya Uchida and Yuta Nakagawa and Naoki Watari and Yuuya Kawasaki},
  journal = {Science Advances},
  year = {2026},
  month = oct,
  doi = {10.1126/sciadv.aed4187},
  url = {https://www.science.org/doi/10.1126/sciadv.aed4187},
  note = {CC BY-NC},
}
RIS
TY  - JOUR
TI  - Optical resolution of H/D isotopic chirality via asymmetric C–H amination
AU  - Tatsuya Uchida
AU  - Yuta Nakagawa
AU  - Naoki Watari
AU  - Yuuya Kawasaki
PY  - 2026
DA  - 2026/10/09
JO  - Science Advances
DO  - 10.1126/sciadv.aed4187
UR  - https://www.science.org/doi/10.1126/sciadv.aed4187
AB  - Isotopic chirality arising from hydrogen/deuterium substitution has long resisted optical resolution because isotopic substitution introduces only minimal stereochemical differences, rendering such molecules structurally pseudo-achiral. Recognizing that the small yet distinct difference in C–H/C–D bond dissociation energies (BDEs) creates an energetic asymmetry, we envisioned that an enantioselective C–H functionalization exploiting this disparity could achieve the kinetic resolution of isotopically chiral molecules. Here, we report a catalytic method for the optical resolution of benzylic and allylic H/D isotopic chirality. This method achieved a remarkably high separation factor ( S = 83.1), enabling the isolation of highly enantioenriched isotopically chiral substrates from racemic mixtures and revealing retention of stereochemical memory during radical recombination in asymmetric C–H functionalization.
SN  - 2375-2548
ER  -