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

Autor:	Cardenas MM; Department of Chemistry and Biochemistry , San Diego State University , 5500 Campanile Drive , San Diego , California 92182-1030 , United States., Toenjes ST; Department of Chemistry and Biochemistry , San Diego State University , 5500 Campanile Drive , San Diego , California 92182-1030 , United States., Nalbandian CJ; Department of Chemistry and Biochemistry , San Diego State University , 5500 Campanile Drive , San Diego , California 92182-1030 , United States., Gustafson JL; Department of Chemistry and Biochemistry , San Diego State University , 5500 Campanile Drive , San Diego , California 92182-1030 , United States.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2018 Apr 06; Vol. 20 (7), pp. 2037-2041. Date of Electronic Publication: 2018 Mar 21.
DOI:	10.1021/acs.orglett.8b00579
Abstrakt:	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 (S N Ar). 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.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu