Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution

The catalytic enantioselective synthesis of 3-aryl-substituted pyrrolopyrimidines (PPYs), a common motif in drug discovery, is achieved through a kinetic resolution via quaternary ammonium salt-catalyzed nucleophilic aromatic substitution (SNAr). Both enantioenriched products and starting materials...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2018-04, Vol.20 (7), p.2037-2041
Main Authors: Cardenas, Mariel M, Toenjes, Sean T, Nalbandian, Christopher J, Gustafson, Jeffrey L
Format: Article
Language:English
Subjects:
Catalysis
Cations
Molecular Structure
Pyrimidines - chemical synthesis
Pyrroles - chemical synthesis
Stereoisomerism
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:The catalytic enantioselective synthesis of 3-aryl-substituted pyrrolopyrimidines (PPYs), a common motif in drug discovery, is achieved through a kinetic resolution via quaternary ammonium salt-catalyzed nucleophilic aromatic substitution (SNAr). Both enantioenriched products and starting materials can be functionalized with no observed racemization to give enantiodivergent access to diverse chiral analogues of an important class of kinase inhibitor. One of the compounds was found to be a potent and selective inhibitor of breast tumor kinase.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00579