Synthesis of Linear (Z)-α,ß-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.
Angew Chem Int Ed Engl
; 55(42): 13210-13214, 2016 10 10.
Article
en En
| MEDLINE
| ID: mdl-27634213
ABSTRACT
Kinetically controlled catalytic cross-metathesis reactions that generate (Z)-α,ß-unsaturated esters selectively are disclosed. A key finding is that the presence of acetonitrile obviates the need for using excess amounts of a more valuable terminal alkene substrates. On the basis of X-ray structure and spectroscopic investigations a rationale for the positive impact of acetonitrile is provided. Transformations leading to various E,Z-dienoates are highly Z-selective as well. Utility is highlighted by application to stereoselective synthesis of the C1-C12 fragment of biologically active natural product (-)-laulimalide.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Acetonitrilos
/
Macrólidos
/
Ésteres
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2016
Tipo del documento:
Article
País de afiliación:
Estados Unidos