Construction of Vicinal Stereocenters via Asymmetric Cyanosilylation

Abstract

Asymmetric cyanosilylation serves as an important tool to convert easily available ketones into cyanohydrins of diverse reactivity. Whereas a large library of organocatalysts and transition-metal catalysts have been identified for monoketones, cyanosilylation of more-complex substrates, particularly those giving enantioenriched vicinal stereocenters, is underexplored in comparison. Here, a pair of recently published kinetic resolution and desymmetrization methods are highlighted for their success in constructing complex vicinal stereocenters by cyanosilylation using tailored aluminum and magnesium catalysts, respectively.

1 Introduction

2 Kinetic Resolution of α-Branched Ketones

3 Desymmetrization of 1,3-Diketones

4 Conclusion

Key words

cyanosilylation - asymmetric catalysis - vicinal stereocenters - quaternary stereocenters - kinetic resolution - desymmetrization

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