Highly Diastereoselective Multicomponent Synthesis of Spirocyclopropyl Oxindoles Enabled by Rare-Earth Metal Salts.
Org Lett
; 25(17): 3001-3006, 2023 May 05.
Article
de En
| MEDLINE
| ID: mdl-37125666
ABSTRACT
The synthesis of polysubstituted spirocyclopropyl oxindoles using a series of rare-earth metal (REM) salts is reported. REMs, in particular Sc(OTf)3, allowed access to the target compounds by a multicomponent reaction with high diastereoselectivity (≤94600). Density functional theory calculations on the model reaction are consistent with the observed selectivity and revealed that the special coordinating capabilities and the oxophilicity of the metal are key factors in inducing the formation of one main diastereoisomer.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Type d'étude:
Prognostic_studies
Langue:
En
Journal:
Org Lett
Sujet du journal:
BIOQUIMICA
Année:
2023
Type de document:
Article
Pays d'affiliation:
Italie