Enantioselective synthesis of 5,6-dihydroindolizines by N-heterocyclic carbene (NHC)-catalyzed core-structure-inspired strategy of azolium-enolate cascade

TitleEnantioselective synthesis of 5,6-dihydroindolizines by N-heterocyclic carbene (NHC)-catalyzed core-structure-inspired strategy of azolium-enolate cascade
Publication TypeJournal Article
Year of Publication2021
AuthorsGhosh, A, Shee, S, Barik, S, Gonnade, RG, Biju, AT
JournalOrganic Letters
Volume23
Issue13
Pagination5223-5228
Date PublishedJUL
Type of ArticleArticle
ISSN1523-7060
AbstractThe core-structure motivated design has allowed the enantioselective synthesis of 5,6-dihydroindolizines via N-heterocyclic carbene (NHC) catalysis. The NHC-catalyzed reaction of alpha,beta-unsaturated aldehydes with the suitably substituted pyrrole derivatives proceed via the initial generation of alpha,beta-unsaturated acylazoliums from enals, and enolates from pyrroles and the reaction culminated in an efficient cascade process involving the Michael-aldol-lactonization-decarboxylation sequence to afford the products in reasonable yields and high selectivities. The method is further extended to the construction of spirocyclic 5,6-dihydroindolizines.
DOI10.1021/acs.orglett.1c01761
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)6.005
Divison category: 
Center for Material Characterization (CMC)

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