High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones
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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Agnieszka Cholewiak1, Kamil Adamczyk, Michał Kopyt
1Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland. pkwiat@chem.uw.edu.pl.
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.
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