Catalytic Enantioselective Synthesis of Spirooxindoles by Oxidative Rearrangement of Indoles. (1st February 2021)

• Record Type: Journal Article
• Authors: Qian, Chenxiao; Li, Pengfei; Sun, Jianwei
• Is Part Of: Angewandte Chemie. Volume 133:Number 11(2021)
• Page Start: 5935
• Page End: 5939
• Publication Date: 2021-02-01
• Subjects: asymmetric catalysis -- heterocycles -- hydrogen bonds -- organocatalysis -- rearrangement; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202015175
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Oxidative rearrangement of indoles to access oxindoles has been used as a key step in complex molecule synthesis. We report a catalytic enantioselective variant of this transformation by chiral phosphoric acid catalysis, providing rapid access to a range of enantioenriched spirooxindoles. The high enantioselectivity is controlled by dynamic kinetic resolution. Abstract : We report a catalytic asymmetric oxidative rearrangement of indoles to oxindoles with high efficiency and enantioselectivity. This process is particularly powerful for the assembly of enantioenriched spirooxindoles, a privileged core structure of natural products.