Enantioselective synthesis of vicinal amino alcohols promoted by fluorine-containing counteranions.

ABSTRACT: Chiral vicinal amino alcohols are pivotal building blocks in organic synthesis and pharmaceutical research. Herein, we report a chiral copper-catalyzed two-step one-pot strategy for the efficient synthesis of diaryl chiral vicinal amino alcohols, featuring excellent diastereoselectivity (>99 : 1 dr) and enantioselectivity (up to 99.5% ee). A key discovery is the critical role of fluorinated counteranions, which significantly enhance both reactivity and stereocontrol-an underappreciated effect in copper-catalyzed asymmetric reactions. DFT calculations reveal that secondary Cu-F interactions, combined with the spatial confinement of hexafluorophosphate, fine-tune the catalytic chiral environment, enabling precise stereocontrol via modulation of π-π stacking and weak non-covalent inter

SUBMITTER: Yang Y 

PROVIDER: S-EPMC12683539 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature