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Enantioselective Insertion of Alkynyl Carbenes into Si-H Bonds: An Efficient Access to Chiral Propargylsilanes and Allenylsilanes

Liang-Liang Yang, Jing Ouyang, Hui-Na Zou, Shou-Fei Zhu* and Qi-Lin Zhou*

*State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China, Email:,

L. L. Yang, J. Ouyang, H.-N. Zou, S.-F. Zhu, Q.-L. Zhou, J. Am. Chem. Soc., 2021, 143, 6401-6406.

DOI: 10.1021/jacs.1c03435

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Chiral spiro phosphate dirhodium complexes catalyze an asymmetric insertion of alkynyl carbenes derived from readily available sulfonylhydrazones into the Si-H bonds of silanes to afford various chiral propargylsilanes with excellent enantioselectivity. Subsequently, a platinum catalyst was used for stereospecific isomerization of the chiral propargylsilanes to the corresponding chiral allenylsilanes.

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Key Words

propargylsilanes, allenes

ID: J48-Y2021