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- Title
Multicomponent Assembly of Complex Oxindoles by Enantioselective Cooperative Catalysis.
- Authors
Hua, Ru‐Yu; Yu, Si‐Fan; Jie, Xiao‐Ting; Qiu, Huang; Hu, Wen‐Hao
- Abstract
Chiral oxindoles are important chemical scaffolds found in many natural products, and their enantioselective synthesis thus attracts considerable attention. Highly diastereo‐ and enantioselective synthetic methods for constructing C3 quaternary oxindoles have been well‐developed. However, the efficient synthesis of chiral 3‐substituted tertiary oxindoles has been rarely reported due to the ease of racemization of the tertiary stereocenter via enolization. Therefore, we herein report on the multicomponent assembly (from N‐aryl diazoamides, aldehydes, and enamines/indoles) of complex oxindoles by enantioselective cooperative catalysis. These reactions proceed under mild conditions and show broad substrate scope, affording the desired coupling products (>90 examples) with good to excellent stereocontrol. Additionally, this research also demonstrates the synthetic potential of this annulation by constructing the 6,6,5‐tricyclic lactone core structure of Speradine A.
- Subjects
ENANTIOSELECTIVE catalysis; OXINDOLES; NATURAL products; ENOLIZATION; RACEMIZATION; ENAMINES
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 51, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202213407