Work

Kinetic Resolution of Acyclic 1,3-Diols by Copper-Catalyzed Regioselective Dehydrogenative Si–O-Coupling

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A nonenzymatic kinetic resolution of acyclic 1,3-diols by regioselective Si–O coupling with a hydrosilane is reported. The in situ-formed Cu–H catalyst with ( R, R )-Ph-BPE as the chiral ligand facilitates the enantioselective silylation of one of the two hydroxy groups. The differentiation between both the enantiomers and the regioisomers strongly depends on the choice of the hydrosilane with a bis(4-anisyl)-substituted tertiary hydrosilane giving the best results. A broad range of anti -1,3-diols is resolved with good to high selectivity factors, especially derivatives bearing a cycloprop-1,1-diyl group at the methylene moiety.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c01543

Authors: Sophie C. Schulze, Martin Oestreich

Institution: Technische Universität Berlin

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Einstein Stiftung Berlin, Technische Universität Berlin