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. 2019 Nov 9;24(22):4058.
doi: 10.3390/molecules24224058.

Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents

Alejandro Torregrosa-Chinillach  1 , Alba Sánchez-Laó  1 , Elisa Santagostino  1 , Rafael Chinchilla  1
Affiliations

Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents

Alejandro Torregrosa-Chinillach et al. Molecules. .

Abstract

A chiral primary amine-salicylamide is used as an organocatalyst for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides and nitroalkenes. The reactions are performed in deep eutectic solvents as reaction media at room temperature, leading to the corresponding adducts with enantioselectivities up to 88% (for maleimides) and 80% (for nitroalkenes). Catalyst and solvent can be recovered and reused.

Keywords: conjugate addition; deep eutectic solvents; maleimides; nitroalkenes; organocatalysis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chiral organocatalysts employed in enantioselective reactions performed in deep eutectic solvents (DESs).
Figure 2
Figure 2
Organocatalyst employed in this study.
See this image and copyright information in PMC

References

    1. Clark J.H., Hunt A., Topi C., Paggiola G., Sherwood J. Sustainable Solvents: Perspectives from Research, Business and International Policy. Royal Society of Chemistry; London, UK: 2017.
    1. Clarke C.J., Tu W.-C., Levers O., Brohl A., Hallett J.P. Green and sustainable solvents in chemical processes. Chem. Rev. 2018;118:747–800. doi: 10.1021/acs.chemrev.7b00571. - DOI - PubMed
    1. Marcus Y. Deep Eutectic Solvents. Springer; Cham, Switzerland: 2019.
    1. García-Alvarez J. Deep eutectic mixtures: Promising sustainable solvents for metal-catalyzed and metal-mediated organic reactions. Eur. J. Inorg. Chem. 2015:5147–5157. doi: 10.1002/ejic.201500892. - DOI
    1. Liu P., Hao J.-W., Mo L.-P., Zhang Z.-H. Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions. RSC Adv. 2015;5:48675–48704. doi: 10.1039/C5RA05746A. - DOI

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