Organic Chemistry Portal

Abstracts

Search:

Alkynylation of Isatin Derivatives Catalyzed by a Silver-Chiral Quaternary Ammonium Salt Derived from Quinine

Xinduo Sun, Chaoji Xiong, Fanrui Zhou, Kun Liang*, Chunhua Wu, Xiaoping Rao and Qian Chen*

*College of Material and Chemical Engineering, Southwest Forestry University, Kunming 650224, China, Email: kliangswfu.edu.cn, chenqianhit.edu.cn

X. Sun, C. Xiong, F. Zhou, K. Liang, C. Wu, X. Rao, Q. Chen, J. Org. Chem., 2023, 88, 7454-7462.

DOI: 10.1021/acs.joc.3c00006


Abstract

A dimeric chiral quaternary ammoniums derived from quinine can be used as cationic inducer of an enantioselective Ag(I)-catalyzed alkynylation of isatin derivatives under mild conditions. The desired chiral 3-alkynyl-3-hydroxy-2-oxindoles can be obtained in good to high yields with excellent enantioselectivites.


see article for more examples


proposed mechanism



Key Words

oxindoles


ID: J42-Y2023