Collect. Czech. Chem. Commun. 2000, 65, 729-740

Stereoconservative Cyanation of [1,1'-Binaphthalene]-2,2'-dielectrophiles. An Alternative Approach to Homochiral C2-Symmetric [1,1'-Binaphthalene]-2,2'-dicarbonitrile and Its Transformations

Peter Kasák and Martin Putala*

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovak Republic


The performed study on the cyanation of [1,1'-binaphthalene]-2,2'-diiodide and [1,1'-binaph- thalene]-2,2'-diyl ditriflate showed reactions with zinc cyanide catalyzed by palladium phosphane complex in DMF to be the most effective procedures with almost complete conservation of stereogenic information - affording corresponding highly enantiomerically enriched dinitrile (from diiodide: 94% yield, 92% ee). Dinitrile was successfully transformed into [1,1'-binaphthalene]-2,2'-dicarboxylic acid and -2,2'-dicarbaldehyde in high yields (84-87%).

Keywords: Axial chirality; Biaryls; Binaphthyl; C2-Symmetry; Cyanation; Aryl halides; Nickel; Palladium; Stereoselective reactions; Triflates.

References: 82 live references.