UV light-driven asymmetric vinylogous aldol reaction of isatins with 2-alkylbenzophenones and enantioselective synthesis of 3-hydroxyoxindoles
Literature Information
Publication Date
2021-12-07
DOI
10.1039/D1QO01555A
Impact Factor
5.281
Authors
Shixuan Cao, Jiatian Li, Taishan Yan, Jie Han
View Original
Abstract
Chiral 3-hydroxyoxindoles are biologically important molecular motifs which are frequently present in natural products and artificial compounds. Herein, we report an ultraviolet light-driven asymmetric vinylogous aldol reaction between versatile isatins and 2-alkylbenzophenones. Under mild conditions, this reaction is catalysed by a chiral amine-derived thiourea, producing chiral 3-hydroxyoxindoles with up to 95% yields and up to 96 : 4 er enantioselectivities with a good substrate scope. Thus, it provides a new and facile method to prepare chiral 3-hydroxyoxindoles. A plausible mechanism is also proposed to rationalize product formation and enantioselectivity.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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