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Asymmetric cyclopropanation of β,γ-unsaturated α-ketoesters with stabilized sulfur ylides catalyzed by C2-symmetric ureas.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2011 Jan 07; Vol. 76 (1), pp. 281-4. Date of Electronic Publication: 2010 Dec 08. - Publication Year :
- 2011
-
Abstract
- A novel organocatalytic asymmetric cyclopropanation of β,γ-unsaturated α-ketoesters with stabilized sulfur ylides using C(2)-symmetric urea as a hydrogen-bond catalyst has been described. This reaction allows an efficient access to 1,2,3-trisubstituted cyclopropane derivatives in moderate to good yields with up to 16:1 dr and 90:10 er under mild reaction conditions. The mechanism study proved that the high stereoinduction originated from the cooperative effect of the hydrogen-bond catalyst.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 76
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 21141872
- Full Text :
- https://doi.org/10.1021/jo101699r