Loading…

The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives

This work involves the synthesis and subsequent development of a number of novel organocatalysts generated from β-amino acids bearing and norbornene skeletons to improve their catalytic characteristics. The aldol reaction between isatin and acetone selected as the model reaction, was used to test an...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2023-06, Vol.13 (28), p.19356-19365
Main Authors: Faragó, Tünde, Remete, Attila M, Szatmári, István, Ambrus, Rita, Palkó, Márta
Format: Article
Language:English
Subjects:
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:This work involves the synthesis and subsequent development of a number of novel organocatalysts generated from β-amino acids bearing and norbornene skeletons to improve their catalytic characteristics. The aldol reaction between isatin and acetone selected as the model reaction, was used to test and study enantioselectivities. The potential impact on enantioselectivity control regarding enantiomeric excess (ee%) was probed by varying the reaction parameters, such as additive, solvent, catalyst loading, temperature and substrate range. The corresponding 3-hydroxy-3-alkyl-2-oxindole derivetives were produced by organocatalyst 7 with good enantioselectivity up to 57% ee in the presence of LiOH. Substrate screening was used to investigate a number of substituted isatins with excellent findings up to 99% ee. Another aspect of this effort involved employing high-speed ball mill apparatus to conduct a mechanochemical study to make this model reaction more environmentally benign and sustainable.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra03528j