Enantioselective synthesis of 5,6-dihydroindolizines by N-heterocyclic carbene (NHC)-catalyzed core-structure-inspired strategy of azolium-enolate cascade
| Title | Enantioselective synthesis of 5,6-dihydroindolizines by N-heterocyclic carbene (NHC)-catalyzed core-structure-inspired strategy of azolium-enolate cascade |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Ghosh, A, Shee, S, Barik, S, Gonnade, RG, Biju, AT |
| Journal | Organic Letters |
| Volume | 23 |
| Issue | 13 |
| Pagination | 5223-5228 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | The core-structure motivated design has allowed the enantioselective synthesis of 5,6-dihydroindolizines via N-heterocyclic carbene (NHC) catalysis. The NHC-catalyzed reaction of alpha,beta-unsaturated aldehydes with the suitably substituted pyrrole derivatives proceed via the initial generation of alpha,beta-unsaturated acylazoliums from enals, and enolates from pyrroles and the reaction culminated in an efficient cascade process involving the Michael-aldol-lactonization-decarboxylation sequence to afford the products in reasonable yields and high selectivities. The method is further extended to the construction of spirocyclic 5,6-dihydroindolizines. |
| DOI | 10.1021/acs.orglett.1c01761 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.005 |
Divison category:
Center for Material Characterization (CMC)