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Enantioselective Addition of Silicon Nucleophiles to Aldimines Using a Preformed NHC–Copper(I) Complex as the Catalyst

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  • This research was supported by the Deutsche Forschungsgemeinschaft (Oe 249/3-2) and the Japanese Society for the Promotion of Science (postdoctoral fellowship to K.N., 2013–2014). M.O. is indebted to the Einstein Foundation (Berlin) for an endowed professorship. We thank Dr. Devendra J. Vyas (Westfälische Wilhelms-Universität Münster) for his initial contributions. NHC=N-heterocyclic carbene.

Abstract

A remaining major challenge in the asymmetric addition of silicon nucleophiles to typical prochiral acceptors, the enantioselective 1,2-addition to aldimines, is addressed. Activation of the Si[BOND]B bond in the silicon pronucleophile by a copper(I) alkoxide with McQuade’s chiral six-membered N-heterocyclic carbene as a supporting ligand releases the silicon nucleophile, which adds to various aldimines with high levels of enantioselectivity. The new method provides a catalytic asymmetric access to α-silylated amines.

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