Construction of Fused Oxabicyclic Scaffolds from Glycals and Styrenes via One-Pot Domino Transformations
Bhardwaj, M; Rasool, F; Tatina, MB; Mukherjee, D
| HERO ID | 5416787 |
|---|---|
| In Press | No |
| Year | 2019 |
| Title | Construction of Fused Oxabicyclic Scaffolds from Glycals and Styrenes via One-Pot Domino Transformations |
| Authors | Bhardwaj, M; Rasool, F; Tatina, MB; Mukherjee, D |
| Journal | Organic Letters |
| Volume | 21 |
| Issue | 9 |
| Page Numbers | 3038-3042 |
| Abstract | Triflic acid catalyzed cascade stereoselective reaction of glycals with styrenes delivers complex oxabicyclic scaffolds such as cis-oxadecalins or cis-cyclopentanofurans simply by tweaking the solvent. In the presence of participating solvents like benzene/toluene, cascade Ferrier C-glycosylation and double Friedel-Crafts reaction leads to densely chiral benzo-fused oxadecalins, whereas in DCM, an unprecedented ring-opening, ring-closing sequence generated cis-cyclopentanofurans. An attempt has been made to explain the above cascade sequences via intermediate trapping, kinetic experiments, and Baldwin's rules. |
| Doi | 10.1021/acs.orglett.9b00234 |
| Pmid | 31013108 |
| Wosid | WOS:000467320000016 |
| Url | https://www.proquest.com/docview/2286929797?accountid=171501&bdid=64576&_bd=pioFb3QmddHIWpeNC7oKLYC1Vgo%3D |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |