Silver-catalyzed [3 + 3]-annulation cascade of alkynyl alcohols and α,β-unsaturated ketones for the regioselective assembly of chromanes
| Title | Silver-catalyzed [3 + 3]-annulation cascade of alkynyl alcohols and α,β-unsaturated ketones for the regioselective assembly of chromanes |
| Publication Type | Journal Article |
| Year of Publication | 2022 |
| Authors | Nakate, AK, Thorat, SS, Jain, S, Krishna, GRama, Vanka, K, Kontham, R |
| Journal | Organic Chemistry Frontiers |
| Volume | 9 |
| Issue | 3 |
| Pagination | 802-809 |
| Date Published | JAN |
| Type of Article | Article |
| ISSN | 2052-4129 |
| Abstract | An 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. |
| DOI | 10.1039/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