Enantioselective synthesis of functionalized β-lactones by NHC-catalyzed aldol lactonization of ketoacids

TitleEnantioselective synthesis of functionalized β-lactones by NHC-catalyzed aldol lactonization of ketoacids
Publication TypeJournal Article
Year of Publication2017
AuthorsMondal, S, Mukherjee, S, Das, TKanti, Gonnade, RG, Biju, AT
JournalJournal of Organic Chemistry
Volume82
Issue17
Date PublishedAUG
Type of ArticleArticle
Abstract

N-Heterocyclic carbene (NHC)-catalyzed intramolecular aldol lactonization of readily available ketoacids leading to the enantioselective synthesis of cyclopentane-fused β-lactones is presented. The reaction proceeds via the generation of NHC-bound enolate intermediates formed from the ketoacids in the presence of the peptide coupling reagent HATU and NHC generated from the chiral triazolium salt. The functionalized β-lactones are formed under mild conditions in high yields and enantioselectivities.

DOI10.1021/acs.joc.7b01526
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.785

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry