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

Authors

Tatsuya Uchida, Yuta Nakagawa, Naoki Watari, Yuuya Kawasaki

Published in

Science advances. Volume 12. Issue 41. Pages eaed4187. Oct 09, 2026. Epub Oct 07, 2026.

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.

PMID:
42842655
Bibliographic data and abstract were imported from PubMed on 08 Oct 2026.

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