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Selective Synthesis of Chiral Carbocycles by Iridium-Catalyzed Asymmetric Mono-, Double-, or Triple Hydrogenation of Cyclic Dienones

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A divergent N,P-iridium-catalyzed asymmetric hydrogenation of cyclic dienones into chiral cyclohexenones, cyclohexanones, or cyclohexanols is described. The π-bonds in cyclic dienones underwent hydrogenation in a sequential manner, favoring the (s)- cis conformed alkene followed by the olefin in the (s)- trans conformation and at last the ketone, to install up to three stereocenters in a single step. The simple choice of the proper catalyst allowed the formation of each respective product in high yield and stereopurity (up to 99% ee, up to 99/1 d.r.). This protocol provides an interesting opportunity to access multiple and stereopure carbocycles starting from the same precursor that otherwise require multistep syntheses.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04476

Authors: Bram B. C. Peters, Jia Zheng, Haili Zhang, Pher G. Andersson

Institutions: Stockholm University, Guangdong Medical College, Southwest Petroleum University

Language: English

Topic: Asymmetric Hydrogenation and Catalysis

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Carl Tryggers Stiftelse för Vetenskaplig Forskning, Knut och Alice Wallenbergs Stiftelse, Stiftelsen Olle Engkvist Byggmästare, Vetenskapsrådet