Enantioselective intramolecular decarboxylative C-H bond func-tionalization of quinazolinones with amino acids by visible light photoredox catalysis

TitleEnantioselective intramolecular decarboxylative C-H bond func-tionalization of quinazolinones with amino acids by visible light photoredox catalysis
Publication TypeJournal Article
Year of Publication2023
AuthorsSonavane, SR, Mhaske, SB
JournalChemistry-An Asian Journal
Volume18
Issue13
Date PublishedJUL
Type of ArticleArticle
ISSN1861-4728
KeywordsC-H functionalization, memory of chirality, Minisci reaction, photodecarboxylative cyclization, photoredox catalysis, quinazolinone alkaloid, Radical
Abstract

The direct visible light-mediated intramolecular decarboxylative C-H functionalization of Csp(2)-H bond adjacent to the nitrogen of a heteroarene has been achieved by iridium-catalyzed photodecarboxylative radical cyclization. This method offers rapid entry to the synthesis of quinazolinone scaffolds from easily accessible starting materials. The newly developed protocol is mild, operationally simple, oxidant free and general. The utility of this unique Csp(3)-Csp(2) bond forming reaction has been demonstrated in the syntheses of Circumdatin, Sclerotigenine and Benzomalvin A class of quinazolinone natural products and their congeners. The present work represents an interesting example of use of memory of chirality in decarboxylative C-C bond forming enantioselective photoredox reaction.

DOI10.1002/asia.202300235
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.1

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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