Diastereoselective three-component vinylogous Mannich reaction of nitrogen heterocycles, acyl/sulfonyl chlorides, and silyloxyfurans/pyrroles.
J Org Chem
; 79(12): 5673-83, 2014 Jun 20.
Article
em En
| MEDLINE
| ID: mdl-24869425
ABSTRACT
A one-step, 3-component vinylogous Mannich reaction of trimethylsilyloxyfuran or N-protected tert-butyldimethylsilyloxypyrrole with a variety of nitrogen-containing heterocycles in the presence of diverse electrophiles is described. The reaction products were generally obtained in high yields and as a single diastereoisomer having the (R*,R*) relative configuration based on crystallographic studies of several derivatives. Several azaheterocycles were successfully used for this reaction, such as isoquinolines, quinoline, phenanthridine, quinazoline, phthalazine, and ß-carboline, and electrophiles included acetyl chloride, methyl chloroformate, methyl chloromalonate, 2-bromobutanoyl chloride, and arylsulfonyl chlorides. The products of the vinylogous Mannich reactions were subjected to further transformations, leading to highly functionalized and stereochemically defined tetracyclic derivatives that are valuable building blocks for the preparation of natural products or medicinal agents.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ácidos Sulfínicos
/
Furanos
/
Compostos Heterocíclicos
/
Nitrogênio
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
França