Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes.
The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic dependence on catalyst concentration and a first-order dependence on epoxide concentration, consistent with a bimetallic pathway involving simultaneous activation of epoxide and cyanide.
Schaus
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Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Jacobsen
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D002384:Catalysis; D002849:Chromatography, Gas; D003486:Cyanides / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D008674:Metals, Rare Earth / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis*
D003486:Cyanides; D004852:Epoxy Compounds; D008674:Metals, Rare Earth; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide