Iron-catalyzed stereoselective C-H alkylation for simultaneous construction of C-N axial and C-central chirality.
Nat Commun
; 15(1): 3503, 2024 Apr 25.
Article
em En
| MEDLINE
| ID: mdl-38664372
ABSTRACT
The assembly of chiral molecules with multiple stereogenic elements is challenging, and, despite of indisputable advances, largely limited to toxic, cost-intensive and precious metal catalysts. In sharp contrast, we herein disclose a versatile C-H alkylation using a non-toxic, low-cost iron catalyst for the synthesis of substituted indoles with two chiral elements. The key for achieving excellent diastereo- and enantioselectivity was substitution on a chiral N-heterocyclic carbene ligand providing steric hindrance and extra represented by noncovalent interaction for the concomitant generation of C-N axial chirality and C-stereogenic center. Experimental and computational mechanistic studies have unraveled the origin of the catalytic efficacy and stereoselectivity.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Nat Commun
Ano de publicação:
2024
Tipo de documento:
Article