HFIP-Promoted Divergent Cycloadditions of Difluoroenoxysilanes with 2-Indolylmethanols: Synthesis of Fluoro 2H-Pyrano[3,4-b]indoles and gem-Difluoro Cyclopenta[b]indoles.
Org Lett
; 26(22): 4610-4615, 2024 Jun 07.
Article
em En
| MEDLINE
| ID: mdl-38780049
ABSTRACT
An oxa-6π-electrocyclization of difluoroenoxysilanes with diaryl 2-indolylmethanols has been developed. In addition, a rarely reported C3-nucleophilic [3+2] cycloaddition of difluoroenoxysilanes with dialkyl 2-indolylmethanols has been disclosed. This divergent cycloaddition approach affording readily available difluoroenoxysilanes as three-atom and C2 synthons provides rapid access to fluoro 2H-pyrano[3,4-b]indoles and gem-difluoro cyclopenta[b]indoles in good to excellent yields with good functional group tolerance. The metal-free and mild conditions using only HFIP as the solvent without any external acid catalyst illuminate practical and environmentally benign advantages.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2024
Tipo de documento:
Article