Enantioselective synthesis of dihydrothiopyranones via NHC- catalyzed [3+3] annulation of 2-bromoenals with beta-oxodithioesters
| Title | Enantioselective synthesis of dihydrothiopyranones via NHC- catalyzed [3+3] annulation of 2-bromoenals with beta-oxodithioesters |
| Publication Type | Journal Article |
| Year of Publication | 2022 |
| Authors | Barik, S, Shee, S, Gonnade, RG, Biju, AT |
| Journal | Organic Letters |
| Volume | 24 |
| Issue | 48 |
| Pagination | 8848-8853 |
| Date Published | DEC |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | The N-heterocyclic carbene (NHC)-organocata-lyzed [3 + 3] annulation of 2-bromoenals with fi-oxodithioesters resulting in the enantioselective synthesis of dihydrothiopyranones is presented. The chiral a,fi-unsaturated acylazoliums generated from 2-bromoenals and carbenes underwent smooth interception with the sulfur nucleophiles to furnish the sulfur heterocycles in satisfactory yields/selectivity. The regioselective formation of dihydrothiopyranones over the competing dihydropyranones is noteworthy. |
| DOI | 10.1021/acs.orglett.2c03642 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.072 |
Divison category:
Center for Material Characterization (CMC)
Database:
Web of Science (WoS)