Enantioselective N-heterocyclic carbene-catalyzed cascade reaction for the synthesis of pyrroloquinolines via N-H functionalization of indoles

TitleEnantioselective N-heterocyclic carbene-catalyzed cascade reaction for the synthesis of pyrroloquinolines via N-H functionalization of indoles
Publication TypeJournal Article
Year of Publication2018
AuthorsMukherjee, S, Shee, S, Poisson, T, Besset, T, Biju, AT
JournalOrganic letters
Volume20
Issue22
Pagination6998-7002
Date PublishedNOV
Type of ArticleArticle
ISSN1523-7060
AbstractFunctionalization of the indole N-H bond for enantioselective synthesis of biologically important pyrroloquinoline derivatives has been reported under oxidative N-heterocyclic carbene catalysis conditions. The interception of catalytically generated chiral alpha,beta-unsaturated acylazoliums with the indole derivatives proceeds in an aza-Michael/Michael/lactonization sequence to deliver the pyrroloquinoline derivatives in good yields, diastereoselectivities, and enantioselectivities. The simultaneous enhancement of reactivity and selectivity observed in polar aprotic solvents is noteworthy.
DOI10.1021/acs.orglett.8b02820
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)6.492
Divison category: 
Organic Chemistry

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