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Kinetic Resolution of BINOLs and Biphenols by Atroposelective, Cu–H-Catalyzed Si–O Coupling with Hydrosilanes

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A nonenzymatic kinetic resolution of monoprotected BINOL and biphenol derivatives by atroposelective Si–O coupling with hydrosilanes is described. The reaction relies on a previously unprecedented Cu–H-catalyzed silylation of phenols. The catalyst system consisting of CuCl, ( R, R )-Ph-BPE, and NaO t Bu enables the enantioselective coupling of the phenolic hydroxy group with a hydrosilane with moderate to good selectivity factors.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03557

Authors: Lisa A. Böser, Martin Oestreich

Institution: Technische Universität Berlin

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Fonds der Chemischen Industrie, Einstein Stiftung Berlin