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Asymmetric Ring Opening of Meso Epoxides with TMSCN Catalyzed by (pybox)lanthanide Complexes

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journal contribution
posted on 16.03.2000, 00:00 by Scott E. Schaus, Eric N. Jacobsen
The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the β-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 simulataneous activation of epoxide and cyanide.