Asymmetric copper-catalyzed synthesis of alpha-amino boronate esters from N-tert-butanesulfinyl aldimines.
J Am Chem Soc
; 130(22): 6910-1, 2008 Jun 04.
Article
em En
| MEDLINE
| ID: mdl-18461938
ABSTRACT
A general and efficient new method for the asymmetric synthesis of alpha-amino boronate esters has been developed. The key step is the Cu(I)-catalyzed addition of bis(pinacolato)diboron to N-tert-butanesulfinyl aldimines, which proceeds in good yields (52-88%) and with very high diastereoselectivities (>962) for a variety of aldimine substrates. This method was applied to an efficient synthesis of bortezomib, a potent alpha-amino boronic acid inhibitor of the proteasome that is in clinical use for the treatment of multiple myeloma and mantle cell lymphoma.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirazinas
/
Ácidos Sulfínicos
/
Ácidos Borônicos
/
Aldeídos
/
Aminas
/
Iminas
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article