Asymmetric Redox Allylic Alkylation to Access 3, 3′‐Disubstituted Oxindoles Enabled by Ni/NHC Cooperative Catalysis. (29th March 2022)

• Record Type: Journal Article
• Authors: Fan, Tao; Song, Jin; Gong, Liu‐Zhu
• Is Part Of: Angewandte Chemie. Volume 134:Number 22(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-29
• Subjects: All-Carbon Quaternary Stereocenters -- Cooperative Catalysis -- N-Heterocyclic Carbene -- Nickel -- Oxindoles; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202201678
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The feasibility of cooperative catalysis between chiral N‐heterocyclic carbenes and nickel in asymmetric reactions has been demonstrated convincingly. The high efficiency of this catalytic system enables the asymmetric allylic alkylation of isatin‐derived enals with allylic carbonates and [3+3] annulation with racemic vinyl epoxides to provide straightforward access to highly enantioenriched 3, 3'‐disubstituted oxindoles. The great practicality of this method in organic synthesis has been showcased by facile product modification and enantioselective synthesis of the key building block to access (−)‐debromoflustramine B. Abstract : Chiral N‐heterocyclic carbene and nickel cooperative catalysis enables asymmetric redox allylic alkylation to access 3, 3′‐disubstituted oxindoles with high enantioselectivity.