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Issue 23, 2018
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High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones

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Abstract

The application of high pressure (up to 9 kbar) allows for relatively fast (1–5 h) and highly enantioselective 1,4-addition of nitromethane and 2-nitropropane to chalcones at room temperature with substantial reduction of catalyst loading (0.2–1 mol% of cinchona alkaloid-based thioureas and squaramides). Various γ-nitroketones were obtained at 9 kbar with high yield and enantioselectivity (up to 98%), whereas in control experiments at atmospheric pressure usually only a small amount (<10%) of products were formed after 20 h.

Graphical abstract: High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones

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Publication details

The article was received on 06 Mar 2018, accepted on 14 May 2018 and first published on 22 May 2018


Article type: Paper
DOI: 10.1039/C8OB00561C
Citation: Org. Biomol. Chem., 2018,16, 4365-4371
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    High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones

    A. Cholewiak, K. Adamczyk, M. Kopyt, A. Kasztelan and P. Kwiatkowski, Org. Biomol. Chem., 2018, 16, 4365
    DOI: 10.1039/C8OB00561C

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