Copper-Mediated Single-Electron Approach to Indoline Amination: Scope, Mechanism, and Total Synthesis of Asperazine A.
J Org Chem
; 87(15): 9907-9914, 2022 08 05.
Article
em En
| MEDLINE
| ID: mdl-35876810
ABSTRACT
Pyrroloindolines bearing a C3-N linkage comprise the core of many biologically active natural products, but many methods toward their synthesis are limited by the sterics or electronics of the product. We report a single electron-based approach for the synthesis of this scaffold and demonstrate high-yielding aminations, regardless of electronic or steric demands. The transformation uses copper wire and isopropanol to promote the reaction. The broad synthetic utility of this heterogeneous copper-catalyzed approach to access pyrroloindolines, diketopiperazine, furoindoline, and (+)-asperazine is included, along with experiments to provide insight into the mechanism of this new process.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Cobre
/
Elétrons
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2022
Tipo de documento:
Article