A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenes the formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d1cc03708k | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenones α,β-unsaturated acyl azoliums.
Chem Commun (Camb)
September 2021
Nicolaus Copernicus University in Torun, Faculty of Chemistry, 7 Gagarin Street, 87-100 Toruń, Poland.
A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenes the formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.
View Article and Find Full Text PDFCatalytic, Enantioselective C2-Functionalization of 3-Aminobenzofurans Using N-Heterocyclic Carbenes.
Org Lett
May 2020
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
N-Heterocyclic carbene catalyzed enantioselective functionalization of 3-aminobenzofurans at the C2-position was realized using 2-bromoenals as the coupling partner. The reaction proceeds via generation of chiral α,β-unsaturated acylazoliums and follows an aza-Claisen rearrangement. The initially formed dihydropyridinone undergoes ring-opening catalyzed by Mg to afford the δ-amino acid derivatives.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!