Oxoammonium Salt-Promoted Multifunctionalization of Saturated Cyclic Amines Based On ß-Oxo Cyclic Iminium Ion Intermediates.
Org Lett
; 24(42): 7839-7844, 2022 Oct 28.
Article
en En
| MEDLINE
| ID: mdl-36264018
ABSTRACT
Herein we describe a convenient method for multiple C(sp3)-H bond functionalization of saturated cyclic amines through oxoammonium salt-promoted oxidation to afford a ß-oxo cyclic iminium ion as a key intermediate, followed by cascade addition with thiocyanate and diverse N-, O-, and S-containing nucleophiles in the green solvent and EtOH. Notably, chiral spiro azapolyheterocycles were prepared enantioselectively (>201 dr, up to 99% ee) when cysteine or serine esters were used as substrates. Moreover, the concise late-stage modification of several natural product derivatives was accomplished using this method.
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Adamantano
/
Aminas
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2022
Tipo del documento:
Article