Concurrent Asymmetric Reactions Combining Photocatalysis and Enzyme Catalysis: Direct Enantioselective Synthesis of 2, 2‐Disubstituted Indol‐3‐ones from 2‐Arylindoles. Issue 1 (3rd December 2018)

• Record Type: Journal Article
• Authors: Ding, Xuan; Dong, Chun‐Lin; Guan, Zhi; He, Yan‐Hong
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 1(2018)
• Page Start: 118
• Page End: 124
• Publication Date: 2018-12-03
• Subjects: asymmetric catalysis -- enzymes -- heterocycles -- photochemistry -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201811085
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The combination of photoredox and enzymatic catalysis for the direct asymmetric one‐pot synthesis of 2, 2‐disubstituted indol‐3‐ones from 2‐arylindoles through concurrent oxidization and alkylation reactions is described. 2‐Arylindoles can be photocatalytically oxidized to 2‐arylindol‐3‐one with subsequent enantioselective alkylation with ketones catalyzed by wheat germ lipase (WGL). The chiral quaternary carbon center at C2 of the indoles was directly constructed. This mode of concurrent photobiocatalysis provides a mild and powerful strategy for one‐pot enantioselective synthesis of complex compounds. The experiments proved that other lipases containing structurally analogous catalytic triad in the active site also can catalyze the reaction in the same way. This reaction is the first example of combining the non‐natural catalytic activity of hydrolases with visible‐light catalysis for enantioselective organic synthesis and it does not require any cofactors. Abstract : Look, no cofactors ! The combination of photoredox and enzymatic catalysis enables the direct asymmetric one‐pot synthesis of C2‐quaternary indolin‐3‐ones from 2‐arylindoles. This reaction is the first example of combining the non‐natural catalytic activity of hydrolases with visible‐light catalysis for enantioselective organic synthesis, and it does not require any cofactors.