Work

Stereoselective Synthesis of 1,n‐Dicarbonyl Compounds Through Palladium‐Catalyzed Ring Opening/Isomerization of Densely Substituted Cyclopropanols

Year: 2024

Type: article

Abstract: We report a highly diastereoselective protocol for the synthesis of 1,4- and 1,5-dicarbonyl compounds from densely substituted cyclopropanols. The methodology involves a palladium-catalyzed ring opening reaction followed by a "metal-walk" and oxidation of a remote hydroxyl group. The methodology represents a new application of cyclopropanols as initiation sites for chain walking remote functionalization. Importantly, this approach provides a straightforward access to highly valuable succinaldehyde derivatives bearing vicinal quaternary and tertiary stereocenters as single diastereomers.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202421476

Authors: Charlotte S. Teschers, Anthony Cohen, Ilan Marek

Institution: Technion – Israel Institute of Technology

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Deutsche Forschungsgemeinschaft, Israel Academy of Sciences and Humanities, Israel Science Foundation