Abstract
Complexes of lanthanide chlorides with pybox ligands catalyze the enantioselective silylcyanation of aromatic and aliphatic aldehydes with ee's of up to 91% under mild and convenient conditions. Studies of catalysts prepared with pybox ligands of varying enantiomeric purity show no marked nonlinear effects, indicating a monometallic transition state. A mechanism for the catalytic reaction is proposed. Crystal structures of [LnCl2(S-Pri-pybox)2][LnCl4(S-Pri-pybox)] (Ln = Eu, Yb) are reported. The structure of the related triflate complex [La(OTf)3(S-Pri-pybox)2] is also reported. Diastereoselectivity has been observed in the reactions of Ln(OTf)3 with racemic Pri-pybox: for Ln = Eu, a heterochiral product containing one R- and one S-pybox ligand is observed, whereas for Ln = Yb a racemic mixture of homochiral bis(pybox) complexes is formed.
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