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

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-04-22 DOI:10.1021/acscatal.5c01543

Sophie C. Schulze, Martin Oestreich

引用次数: 0

Abstract

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.

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.