Work

Chiral Transient Directing Groups for Catalytic Asymmetric Intramolecular Alkene Hydroacylation

Year: 2025

Type: article

Abstract: We developed a chiral 2-aminopyridine as a co-catalyst with Rh(I) to accomplish highly enantioselective intramolecular alkene hydroacylation reactions (up to 96:4 er). The chiral 2-aminopyridine served dual purposes: a transient directing group for aldehyde C–H activation and the sole source of asymmetry in the transformation. Our chiral transient directing group approach overcame prior limitations in asymmetric hydroacylation reactions, where reactants containing embedded chelating groups were required for success. We demonstrated our method in enantioselective syntheses of two biologically-relevant small molecules.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c02922

Authors: Parker B. Staub, Hannah M. Holst, Nitha N. Puthalath, Christopher J. Douglas

Institution: University of Minnesota

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Office of the Vice President for Research, University of Minnesota, University of Minnesota

Awards: G1312912843, G4798449191