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

Authors :
Sun X
Xiong C
Zhou F
Liang K
Wu C
Rao X
Chen Q
Source :
The Journal of organic chemistry [J Org Chem] 2023 Jun 02; Vol. 88 (11), pp. 7454-7462. Date of Electronic Publication: 2023 May 23.
Publication Year :
2023

Abstract

Asymmetric addition of terminal alkynes catalyzed by a transition metal to isatins obviously is an efficient and economic method for the synthesis of 3-alkynyl-3-hydroxy-2-oxindoles. The new dimeric chiral quaternary ammoniums derived from a natural chiral alkaloid, quinine, can be used as cationic inducers of the enantioselectivity for the 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 high to excellent enantioselectivites (≤99% ee). A variety of aryl-substituted terminal alkynes and substituted isatins are tolerated in this reaction.

Details

Language :
English
ISSN :
1520-6904
Volume :
88
Issue :
11
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
37219935
Full Text :
https://doi.org/10.1021/acs.joc.3c00006