1. Highly diastereoselective Hydrocyanation of α-sulfinyl cycloalkanones
- Author
-
Ana M. Martin Castro, José L. García Ruano, Ana Escribano, and J. H. Rodriguez
- Subjects
Reaction mechanism ,Organic Chemistry ,chemistry.chemical_element ,Cyclohexanone ,Biochemistry ,Sulfur ,Acid catalysis ,chemistry.chemical_compound ,chemistry ,Drug Discovery ,Hydrocyanation ,Organic chemistry ,Stereoselectivity ,Lewis acids and bases ,Cyanohydrin - Abstract
Hydrocynation of cyclic α-sulfinyl ketones under different conditions has been studied. The obtained results show that compounds derived from cyclohexanone react with Et2AlCN yielding only sulfinyl cyanohydrins exhibiting different configurations at sulfur and at hydroxylic carbon. The stereoselectivity is lightly lower but also very high starting from α-sulfinyl cyclopentanones. The influence of Lewis acids as well as the stereochemical course of these reactions have also been discussed.
- Published
- 1994