Catalyst-controlled chemoselective reaction of 3-indolylmethanols with cyclic enaminones leading to C2-functionalized indoles.
J Org Chem
; 80(3): 1841-8, 2015 Feb 06.
Article
in En
| MEDLINE
| ID: mdl-25561356
ABSTRACT
A catalyst-controlled chemoselective formal 1,2-addition of 3-indolylmethanols with cyclic enaminones has been established in the presence of TfOH as a strong acid, which afforded C2-functionalized indole derivatives in generally good yields (up to 89% yield). This reaction not only confronted the great challenge in 1,2-addition of 3-indolylmethanols but also provided a good strategy for C2-functionalization of indole derivatives. The investigation on the reaction mechanism revealed that this formal 1,2-addition included a tandem sequence of 1,4-addition/[1,3]-C migration/isomerization, in which the [1,3]-C migration of the 1,4-addition product was a key step and the acidity of the catalyst played a decisive role in the observed chemoselectivity.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Indoles
Language:
En
Journal:
J Org Chem
Year:
2015
Document type:
Article
Affiliation country:
China