Cyclization via carbolithiation of alpha-amino alkyllithium reagents.
Org Lett
; 10(18): 4017-20, 2008 Sep 18.
Article
em En
| MEDLINE
| ID: mdl-18700774
ABSTRACT
We report a new route to tertiary alpha-amino stereocenters by sequential alkylation of alpha-amino nitriles followed by reductive lithiation of the nitrile and cyclization onto an alkene. Reductive lithiation of alpha-amino nitriles using lithium 4,4'-di-tert-butylbiphenylide (LiDBB) and subsequent intramolecular carbolithiation proceeded with modest to high diastereoselectivity to deliver cyclic or spirocyclic ring systems. The stereoselectivity of these intramolecular carbolithiations was examined using density function calculations to evaluate plausible transition state models.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Carbono
/
Aminas
/
Indicadores e Reagentes
/
Lítio
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2008
Tipo de documento:
Article
País de afiliação:
Estados Unidos