Highly enantioselective carbene insertion into N-H bonds of aliphatic amines.
Science
; 366(6468): 990-994, 2019 11 22.
Article
en En
| MEDLINE
| ID: mdl-31753998
ABSTRACT
Aliphatic amines strongly coordinate, and therefore easily inhibit, the activity of transition-metal catalysts, posing a marked challenge to nitrogen-hydrogen (N-H) insertion reactions. Here, we report highly enantioselective carbene insertion into N-H bonds of aliphatic amines using two catalysts in tandem an achiral copper complex and chiral amino-thiourea. Coordination by a homoscorpionate ligand protects the copper center that activates the carbene precursor. The chiral amino-thiourea catalyst then promotes enantioselective proton transfer to generate the stereocenter of the insertion product. This reaction couples a wide variety of diazo esters and amines to produce chiral α-alkyl α-amino acid derivatives.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Técnicas de Química Sintética
/
Aminas
/
Metano
Idioma:
En
Revista:
Science
Año:
2019
Tipo del documento:
Article
País de afiliación:
China