Journal of Organic Chemistry p. 5179 - 5183 (1994)
Update date:2022-08-28
Topics:
Engman, Lars
Stern, David
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 conditions.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 benzeneselenolate 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.
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