L. Engman, D. Stern
Sep 1, 1994
Citations
0
Influential Citations
33
Citations
Journal
Journal of Organic Chemistry
Abstract
In the presence of N-acetylcysteine sodium salt, benzeneselenolate ion was generated in situ from diphenyl diselenide via thiol/diselenide and thiol/selenenyl sulfide exchange in aqueous methanol under mild condi- tions. Benzeneselenolate ion thus formed was efficiently alkylated and arylated to afford alkyl phenyl selenides and aryl phenyl selenides, respectively. α,β-Epoxy ketones were catalytically reduced by benzene- selenolate ion to afford β-hydroxy ketones (aldols) in good yields. The stereospecificity of the reaction was demonstrated in the preparation of optically active β-hydroxy ketones from chiral α,β-epoxy ketones