Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF3-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles.
J Org Chem
; 89(2): 1147-1159, 2024 Jan 19.
Article
em En
| MEDLINE
| ID: mdl-38175524
ABSTRACT
An expedient and efficient synthetic method for the divergent synthesis of 1-trifluoromethylated cyclopenta[b]indoles that relies on Brønsted acid-catalyzed dehydrative Nazarov-type cyclization of CF3-substituted 3-indolylallyl alcohols is described. Two classes of 1-trifluoromethylated cyclopenta[b]indoles can be easily accessed simply by changing the NH-protecting group of indoles. With arylsulfonyl protected 3-indolylallyl alcohols as starting materials, the reaction provided the arylsulfonyl protected 1-trifluoromethylated cyclopenta[b]indoles in good to excellent yields, whereas pivaloyl (Piv) protected substrates led to the formation of NH-free 1-trifluoromethylated cyclolopenta[b]indoles with another alkenyl isomer. This protocol features tunable chemoselectivity, operational simplicity, excellent functional group compatibility, and mild metal-free conditions.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China