Enantiodivergent Synthesis of (+)- and (-)-Pyrrolidineâ
197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination.
Chemistry
; 22(43): 15529-15535, 2016 Oct 17.
Article
en En
| MEDLINE
| ID: mdl-27624405
ABSTRACT
A highly efficient, diastereoselective, iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving α-substituted amino alkenes is described. Thus, enantiopure trans-2,5-disubstituted pyrrolidines and trans-5-substituted proline derivatives were synthesized by means of a combination of enantiopure starting materials, easily available from l-α-amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (-)-pyrrolidineâ
197B alkaloids from l-glutamic acid. In addition, a computational study was carried out to gain insight into the complete diastereoselectivity of the transformation.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Pirrolidinas
/
Compuestos Férricos
/
Ácido Glutámico
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2016
Tipo del documento:
Article
País de afiliación:
España