Issue 14, 2023

Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters

Abstract

Indoline skeletons are widely found in many natural isolates and pharmaceuticals, making indoline synthesis an ongoing research hotspot in synthetic chemistry. However, the catalytic asymmetric de novo construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we present a solution to this unmet challenge through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, which are formed in situ by photoinduced carbene transfer. As a result, a wide range of chiral indolines bearing C2-quaternary stereocenters are obtained with good enantio- and diastereoselectivities (up to 19 : 1 dr and 96 : 4 er).

Graphical abstract: Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters

Supplementary files

Article information

Article type
Research Article
Submitted
14 abr 2023
Accepted
28 mai 2023
First published
02 jun 2023

Org. Chem. Front., 2023,10, 3498-3503

Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters

B. Qu, B. Shi, L. He, J. Shi, W. Xiao and L. Lu, Org. Chem. Front., 2023, 10, 3498 DOI: 10.1039/D3QO00551H

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