Silver-catalyzed [3 + 3]-annulation cascade of alkynyl alcohols and α,β-unsaturated ketones for the regioselective assembly of chromanes

TitleSilver-catalyzed [3 + 3]-annulation cascade of alkynyl alcohols and α,β-unsaturated ketones for the regioselective assembly of chromanes
Publication TypeJournal Article
Year of Publication2022
AuthorsNakate, AK, Thorat, SS, Jain, S, Krishna, GRama, Vanka, K, Kontham, R
JournalOrganic Chemistry Frontiers
Volume9
Issue3
Pagination802-809
Date PublishedJAN
Type of ArticleArticle
AbstractAn unprecedented Ag(i)-catalyzed [3 + 3]-annulation of alkynyl alcohols (5-hexyn-1-ols) and α,β-unsaturated ketones is reported to construct simple to complex chromanes. This transformation begins with hydroalkoxylation of alkynol through C–C triple bond activation to give cyclic-enol ether, followed by intermolecular 1,4-addition and intramolecular 1,2-addition of enol ethers onto the enone and oxidative aromatization or Grob-type elimination steps. Facile reaction conditions, broad substrate scope, good to excellent yields, and atom economy are the salient features of this protocol. Isolation of the active pyran-tethered cyclohexadiene reaction intermediate, additional supporting experiments, and DFT calculations strongly support the experimental findings and corroborate our proposed mechanism.
DOI10.1039/D1QO01643A
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)5.281
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry

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