Unveiling a Strategy for Ring Opening of Epoxides: Synthesis of 2-Hydroxyindolinylidenes Using α-Ester Sulfoxonium Ylides.
Org Lett
; 26(5): 1034-1039, 2024 Feb 09.
Article
em En
| MEDLINE
| ID: mdl-38286095
ABSTRACT
The untapped potential of α-carbonyl sulfoxonium ylides in epoxide ring-opening reactions has been a notable gap in current research, with such reactivity predominantly associated with the highly reactive dimethylsulfoxonium methylide. This study introduces an innovative approach wherein an epoxide indole, formed in situ from 2-hydroxyindoline-3-triethylammonium bromide, undergoes reaction with α-ester sulfoxonium ylides. The outcome is the efficient synthesis of a range of 2-hydroxyindolin-3-ylidenes, demonstrating favorable yields (41-81%) and Z/E ratios from 41 to those of exclusive Z isomers. Additionally, the photophysical properties of the synthesized indolinylidenes are explored, along with their derivatization using various nucleophiles under acid catalysis.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Brasil