Work

Access to Enantioenriched 1, n ‐Diols by Cu‐Catalyzed Enantioselective Protoboration and Hydroboration of Alkenyl Ethers

Year: 2025

Type: article

Abstract: We report two catalytic enantioselective borylation/oxidation sequences that streamline access to either enantioenriched 1,2‐ or 1,3‐diols starting from O ‐benzyl‐protected allylic alcohols as a single precursor. The approach takes advantage of the complementary regioselectivity of the Cu‐catalyzed protoboration and the Cu‐catalyzed hydroboration of disubstituted alkenes, which effectively install a borane function and a hydrogen atom on opposite C(sp 2 ) carbon atoms of a carbon–carbon double bond. The two methods feature broad substrate scope and are amenable to large scale without measurable loss of the catalytic efficiency. Both protocols display high levels of regioselectivity and enantioselectivity.

Source: Helvetica Chimica Acta

DOI: 10.1002/hlca.202500009

Authors: Arthur Flaget, Orlando Cesa, Clément Mazet

Institution: University of Geneva

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,030

Funders: National Science Foundation, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung, Université de Genève