Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji-Trost Process.
Chemistry
; 26(63): 14330-14334, 2020 Nov 11.
Article
em En
| MEDLINE
| ID: mdl-32812670
ABSTRACT
A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C-N bond cleavage followed by ß-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Ano de publicação:
2020
Tipo de documento:
Article