Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles

An efficient palladium-catalyzed intramolecular deacetylative dearomatization reaction of 3-acetoxyindoles has been developed. A range of tetracyclic indolin-3-ones bearing C2-quaternary stereocenters are achieved in good yields, showing a wide substrate scope for this reaction. A preliminary enanti...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2019-05, Vol.9 (25), p.13959-13967
Main Authors: Liang, Ren-Xiao, Wang, Ke, Song, Ling-Jie, Sheng, Wei-Jian, Jia, Yi-Xia
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Enantiomers
Indoles
Palladium
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient palladium-catalyzed intramolecular deacetylative dearomatization reaction of 3-acetoxyindoles has been developed. A range of tetracyclic indolin-3-ones bearing C2-quaternary stereocenters are achieved in good yields, showing a wide substrate scope for this reaction. A preliminary enantioselective reaction is established to furnish the product in 63% ee by using ( , , )-phosphoramide-PE as a chiral ligand.
ISSN:2046-2069
2046-2069
DOI:10.1039/c9ra02569c