Efficient Construction of Novel C3-Silyl Substituted Chiral Proline Catalysts

doi:10.16183/j.cnki.jsjtu.2021.038

Abstract

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

CLC Number:

O621.3

TAN Fuxin, LI Zihao, ZHOU Jia, ZHANG Shuyu. Efficient Construction of Novel C3-Silyl Substituted Chiral Proline Catalysts[J]. Journal of Shanghai Jiao Tong University, 2021, 55(9): 1058-1063.

Figures/Tables 5

References 37

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