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Synlett 2024; 35(12): 1327-1332
DOI: 10.1055/a-2160-7887
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Construction of Vicinal Stereocenters via Asymmetric Cyanosilylation

Zhongxing Huang  ∗
a   State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. of China
› Author AffiliationsWe thank the National Natural Science Foundation of China (no. 22171238), Research Grants Council of Hong Kong (nos. 27301821, 17304523) for financial support. We acknowledge funding support from the Laboratory for Synthetic Chemistry and Chemical Biology under the Health@InnoHK Program launched by the Innovation and Technology Commission, the Government of HKSAR.
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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


Publication History

Received: 09 August 2023

Accepted after revision: 25 August 2023

Accepted Manuscript online:
25 August 2023

Article published online:
05 October 2023

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