Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes |
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Authors: | Schaus S E Jacobsen E N |
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Affiliation: | Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. |
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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. |
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