Amines bearing tertiary substituents by tandem enantioselective carbolithiation-rearrangement of vinylureas.
Org Lett
; 15(1): 34-7, 2013 Jan 04.
Article
em En
| MEDLINE
| ID: mdl-23252812
ABSTRACT
In the presence of (-)-sparteine or a (+)-sparteine surrogate, organolithiums add to N-alkenyl-N'-arylureas to give benzylic organolithiums in an enantioselective manner. Under the influence of DMPU, these organolithiums undergo rearrangement with migration of the N'-aryl ring from N to C, leading to the urea derivatives of enantiomerically enriched amines bearing tertiary substituents. Basic hydrolysis returns the functionalized amine, providing a new synthetic route to compounds with quaternary stereogenic centers bearing nitrogen.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Esparteína
/
Ureia
/
Compostos de Vinila
/
Aminas
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article