A Missing Link in Multisubstituted Pyrrolidines: Remote Stereocontrol Forged by Rhodium-Alkyl Nitrene.
Angew Chem Int Ed Engl
; 61(47): e202212421, 2022 11 21.
Article
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| MEDLINE
| ID: mdl-36202757
ABSTRACT
Pyrrolidines are significant N-heterocycles in medicinal chemistry and are among the top ten ring systems found in drug molecules. While simple derivatives are commercially available, densely decorated derivatives with precise stereochemical arrangements remain difficult to obtain. Methods for synthesizing multisubstituted pyrrolidines with nonadjacent stereocenters are particularly scarce. To bridge this gap, we report the stereoselective synthesis of remotely decorated, trisubstituted ß-prolines via Rh-catalyzed C-H amination. The transformation proceeds well in the presence of various functionalities with exclusive anti-selectivity. Carboxylic acids in the products serve as gateways for diverse downstream transformations. Furthermore, the combined experimental and computational study sheds lights on the origin of high diastereoselectivity.
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01-internacional
Base de datos:
MEDLINE
Asunto principal:
Rodio
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2022
Tipo del documento:
Article
País de afiliación:
Japón