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Issue 14, 2018
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Chiral copper-salen complex grafted over functionalized mesoporous silica as an efficient catalyst for asymmetric Henry reactions and synthesis of the potent drug (R)-isoproterenol

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Abstract

Synthesis of enantiomerically pure drug molecules using functionalized mesoporous materials bearing a chiral moiety is a longstanding goal in heterogeneous catalysis. Herein, we report an efficient and enantioselective one-pot Henry reaction over a highly ordered functionalized mesoporous silica-supported chiral copper-salen catalyst, Cu(II)@AFS-1, in DCM at RT. The catalyst was characterized by UV-Vis, FT-IR spectroscopy, PXRD, N2 adsorption/desorption, HR-TEM, EPR, and thermogravimetric and elemental analyses. The diastereoselective Henry reaction of nitroethane was carried out by using this catalyst to obtain good yields (up to 96%) and ee (up to 95%) of β-nitroalcohols with acceptable dr (3.2 : 1). Additionally, the enantiomerically pure drug (R)-(−)-isoproterenol can be synthesized through the asymmetric Henry reaction of 3,4-dimethoxybenzaldehyde over this chiral mesoporous Cu-catalyst as a key step.

Graphical abstract: Chiral copper-salen complex grafted over functionalized mesoporous silica as an efficient catalyst for asymmetric Henry reactions and synthesis of the potent drug (R)-isoproterenol

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Publication details

The article was received on 11 Apr 2018, accepted on 07 Jun 2018 and first published on 07 Jun 2018


Article type: Paper
DOI: 10.1039/C8NJ01745J
Citation: New J. Chem., 2018,42, 11896-11904
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    Chiral copper-salen complex grafted over functionalized mesoporous silica as an efficient catalyst for asymmetric Henry reactions and synthesis of the potent drug (R)-isoproterenol

    M. Halder, P. Bhanja, Md. M. Islam, A. Bhaumik and Sk. M. Islam, New J. Chem., 2018, 42, 11896
    DOI: 10.1039/C8NJ01745J

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