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Asymmetric meso-epoxide ring-opening with trimethylsilyl cyanide promoted by chiral binuclear complexes of titanium. Dichotomy of C-C versus C-N bond formation

Lookup NU author(s): Professor Michael North

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Abstract

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. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Publication metadata

Author(s): Belokon Y, Chusov D, Peregudov A, Yashkina L, Timofeeva G, Maleev V, North M, Kagan H

Publication type: Article

Publication status: Published

Journal: Advanced Synthesis and Catalysis

Year: 2009

Volume: 351

Issue: 18

Pages: 3157-3167

ISSN (print): 1615-4150

ISSN (electronic): 1615-4169

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/adsc.200900523

DOI: 10.1002/adsc.200900523

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