Enantioselective organocatalytic approach to the synthesis of alpha,alpha-disubstituted cyanosulfones
- Resource Type
- Authors
- Jesús López-Cantarero; José L. García Ruano; Sara Duce; M. Belén Cid
- Source
- The Journal of organic chemistry. 74(1)
- Subject
- chemistry.chemical_classification
Ketone
Nitrile
Molecular Structure
Chemistry
Cinchona Alkaloids
Organic Chemistry
Enantioselective synthesis
Stereoisomerism
Cinchonine
Ketones
Chemical synthesis
Catalysis
chemistry.chemical_compound
Michael reaction
Organic chemistry
Sulfones
Cinchonidine
- Language
- ISSN
- 1520-6904
Optically pure cyano tert-alkyl sulfones have been obtained by organocatalytic enantioselective Michael addition of alpha-substituted cyanosulfones to vinyl ketones using cinchona alkaloids as catalysts. The best results were obtained for p-trifluorophenylsulfones by using VIII as catalyst in toluene at -40 degrees C. Reactions proved to be applicable for a variety of alpha,beta-unsaturated ketones, affording alpha,alpha-disubstituted cyanosulfones in excellent yields with er's up to 90:10.