Work

Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1 H )-Quinolones Induced by Visible Light Irradiation

Year: 2016

Type: article

Abstract: In the presence of a chiral thioxanthone catalyst (10 mol %) the title compounds underwent a clean intermolecular [2 + 2] photocycloaddition with electron-deficient olefins at λ = 419 nm. The reactions not only proceeded with excellent regio- and diastereoselectivity but also delivered the respective cyclobutane products with significant enantiomeric excess (up to 95% ee). Key to the success of the reactions is a two-point hydrogen bonding between quinolone and catalyst enabling efficient energy transfer and high enantioface differentiation. Preliminary work indicated that solar irradiation can be used for this process and that the substrate scope can be further expanded to isoquinolones.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6b03221

Authors: Andreas Tröster, Rafael Alonso, Andreas Bauer, Thorsten Bach

Institution: Technical University of Munich

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Alexander von Humboldt-Stiftung, European Commission, Deutsche Forschungsgemeinschaft, European Research Council