Enantioselective N-heterocyclic carbene-catalyzed cascade reaction for the synthesis of pyrroloquinolines via N-H functionalization of indoles
| Title | Enantioselective N-heterocyclic carbene-catalyzed cascade reaction for the synthesis of pyrroloquinolines via N-H functionalization of indoles |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Mukherjee, S, Shee, S, Poisson, T, Besset, T, Biju, AT |
| Journal | Organic letters |
| Volume | 20 |
| Issue | 22 |
| Pagination | 6998-7002 |
| Date Published | NOV |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | Functionalization of the indole N-H bond for enantioselective synthesis of biologically important pyrroloquinoline derivatives has been reported under oxidative N-heterocyclic carbene catalysis conditions. The interception of catalytically generated chiral alpha,beta-unsaturated acylazoliums with the indole derivatives proceeds in an aza-Michael/Michael/lactonization sequence to deliver the pyrroloquinoline derivatives in good yields, diastereoselectivities, and enantioselectivities. The simultaneous enhancement of reactivity and selectivity observed in polar aprotic solvents is noteworthy. |
| DOI | 10.1021/acs.orglett.8b02820 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.492 |
Divison category:
Organic Chemistry