Issue 41, 2022

Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper catalyzed asymmetric propargylation

Abstract

Herein, a copper catalyzed asymmetric propargylation of 2-oxindole-3-carboxylate esters with terminal propargylic esters is described. This strategy successfully provides a direct approach to constructing a broad range of chiral C3-tetrasubstituted oxindoles with contiguous tertiary and quaternary carbon stereocenters in high yields and excellent enantioselectivities (16 examples, up to 99% yield and 98% ee). Moreover, the diastereoisomers of the two newly formed stereocenters can be separated by silica gel chromatography, thereby providing a valuable stereoselective access to all four possible stereoisomers of C3-tetrasubstituted oxindoles.

Graphical abstract: Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper catalyzed asymmetric propargylation

Supplementary files

Article information

Article type
Paper
Submitted
24 jul 2022
Accepted
10 sep 2022
First published
21 sep 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 26727-26732

Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper catalyzed asymmetric propargylation

J. Wang, Y. Zhao, C. Yao and K. Zhang, RSC Adv., 2022, 12, 26727 DOI: 10.1039/D2RA04603B

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