Related Experiment Videos
Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes
1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Organic Letters
|April 18, 2000
Abstract:
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.