Nitro-Enabled Atroposelective Dynamic Kinetic Resolution of 2-Arylindoles by Phase-Transfer Catalysis.
Org Lett
; 26(3): 681-686, 2024 Jan 26.
Article
in En
| MEDLINE
| ID: mdl-38232328
ABSTRACT
This study presents the atroposelective alkylation of 2-arylindoles catalyzed by a substituted cinchonium salt as a phase-transfer catalyst. Under the optimized reaction conditions, various substrates are employed to yield products with high enantioselectivity. The presence of an ortho-nitro group at the aromatic ring is essential for high atroposelectivity, because it facilitates favorable interactions between the catalyst and substrate. The origin of the enantioselectivity reveals favorable π-π interactions for both enantiomers and unfavorable steric strains for undesired enantiomers.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2024
Document type:
Article