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

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Title: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
Creators:
Kasák, Peter
Putala, Martin
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 5, pp. 729-740
Uncontrolled Keywords:Biaryls, Nickel, Aryl halides, Triflates, Cyanation, Binaphthyl, <i>C</i><sub>2</sub>-Symmetry, Stereoselective reactions, Palladium, Axial chirality

Abstract

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%). <p>

Title: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
Creators:
Kasák, Peter
Putala, Martin
Uncontrolled Keywords:Biaryls, Nickel, Aryl halides, Triflates, Cyanation, Binaphthyl, <i>C</i><sub>2</sub>-Symmetry, Stereoselective reactions, Palladium, Axial chirality
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:5
Page Range:pp. 729-740
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000729UNSPECIFIED
ID Code:1675
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Kasák, Peter; Putala, Martin (2000) 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. Collection of Czechoslovak Chemical Communications, 65 (5). pp. 729-740. ISSN 0010-0765

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