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

作者:Belokon Yuri N*; Chusov Denis; Peregudov Alexander S; Yashkina Lidia V; Timofeeva Galina I; Maleev Victor I; North Michael; Kagan Henri B
来源:Advanced Synthesis & Catalysis, 2009, 351(18): 3157-3167.
DOI:10.1002/adsc.200900523

摘要

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.

  • 出版日期2009-12