Chromium-Catalyzed Stereodivergent Carbonyl Addition Dictated by Non-Covalent Interactions.

Authors

Tianbing Yao, Mingyang Bi, Zhaobin Wang

Published in

Angewandte Chemie (International ed. in English). Pages e9365925. Aug 05, 2026. Epub Aug 05, 2026.

Abstract

Catalytic stereodivergent synthesis, which accesses the full complement of stereoisomers from a common precursor set, is a paramount objective in drug discovery. However, achieving this control via radical-involved pathways remains a formidable frontier due to the transient nature of open-shell intermediates. Here, we report a unified chromium-catalyzed platform that harnesses a radical-polar crossover mechanism to achieve the fully ligand-controlled stereodivergent synthesis of chiral β-fluoro alcohols. We demonstrate that the stereochemical outcome is not inherent to the substrate but is dictated by the ancillary ligand through distinct non-covalent interactions: a chiral bisoxazoline ligand enforces a rigid transition state via fluorine-mediated hydrogen bonding to selectively deliver syn-diastereomers, whereas a chemically distinct pyridine-imidazoline ligand exploits electronic desymmetrization via π-π stacking to invert selectivity toward anti-isomers. Notably, this protocol enables the programmable assembly of all four stereoisomers of fluorosugar derivatives.

PMID:
42554512
Bibliographic data and abstract were imported from PubMed on 05 Aug 2026.

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