Asymmetric meso-Epoxide Ring-Opening with Trimethylsilyl Cyanide Promoted by Chiral Binuclear Complexes of Titanium. Dichotomy of CC versus CN Bond Formation

In the presence of chiral catalysts derived from the same chiral hexadentate ligand and aluminium, zinc or titanium ions, the reaction between cyclohexene oxide and trimethylsilyl cyanide can be controlled to give predominantly either the nitrile (up to 99% ee) or the isonitrile product (up to 94% e...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-12, Vol.351 (18), p.3157-3167
Main Authors: Belokon, Yuri N., Chusov, Denis, Peregudov, Alexander S., Yashkina, Lidia V., Timofeeva, Galina I., Maleev, Victor I., North, Michael, Kagan, Henri B.
Format: Article
Language:English
Subjects:
asymmetric ring-opening
binuclear catalysts
meso-epoxides
N/C dichotomy
trimethylsilyl cyanide
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Summary:In the presence of chiral catalysts derived from the same chiral hexadentate ligand and aluminium, zinc or titanium ions, the reaction between cyclohexene oxide and trimethylsilyl cyanide can be controlled to give predominantly either the nitrile (up to 99% ee) or the isonitrile product (up to 94% ee). The metal ion, ligand stereochemistry and base concentration all play a role in determining the product ratio.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900523