Phthalides by rhodium-catalyzed ketone hydroacylation.
J Am Chem Soc
; 131(43): 15608-9, 2009 Nov 04.
Article
en En
| MEDLINE
| ID: mdl-19813746
ABSTRACT
Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO(3), OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Ácidos Ftálicos
/
Rodio
Idioma:
En
Revista:
J Am Chem Soc
Año:
2009
Tipo del documento:
Article
País de afiliación:
Canadá