Journal of Shanghai Jiao Tong University

Journal of Shanghai Jiaotong University >

2021 , Vol. 55 >Issue 9: 1058 - 1063

DOI: https://doi.org/10.16183/j.cnki.jsjtu.2021.038

Efficient Construction of Novel C3-Silyl Substituted Chiral Proline Catalysts

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  • Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai 200240, China

Received date: 2021-02-05

  Online published: 2021-06-08

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Abstract

In order to apply the C-H activation strategy to the development of chiral organic catalysts, two novel C3-trimethylsilyl substituted chiral proline catalysts are designed and synthesized using L-proline as the starting material and C(sp 3)-H silylation as the key step, which are applied to the asymmetric aldol reaction of p-nitrobenzaldehyde with acetone and the asymmetric Mannich reaction of imine with β-methylbutyraldehyde, respectively. Both target products can be synthesized with a good enantioselectivity. This strategy effectively enriches the means of structural modification of proline and provids a new method for the development of new silicon-containing organic catalysts.

Key words： C(sp3)-H silylation; proline; organic catalysis

Cite this article

TAN Fuxin, LI Zihao, ZHOU Jia, ZHANG Shuyu . Efficient Construction of Novel C3-Silyl Substituted Chiral Proline Catalysts[J]. Journal of Shanghai Jiaotong University, 2021 , 55(9) : 1058 -1063 . DOI: 10.16183/j.cnki.jsjtu.2021.038

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