Abstract
The isosteviol derived bifunctional primary amine-squaramide organocatalysts were applied in the Michael addition between nitroalkenes and acetophenone. The conjugate addition isomers of two configurations were observed with high yields (up to 93% yield) and good enantioselectivity (up to 91% ee) at room temperature.
Keywords: Isosteviol, asymmetric catalysis, organocatalyst, squaramide, michael reaction, nitroalkenes.
Graphical Abstract
[http://dx.doi.org/10.1002/chem.201301996] [PMID: 24115407]
[http://dx.doi.org/10.1002/chem.201601844] [PMID: 27465662]
[http://dx.doi.org/10.1039/C6CS00247A] [PMID: 28221384]
[http://dx.doi.org/10.1021/cr068373r] [PMID: 18072808]
[http://dx.doi.org/10.1002/chem.200501076] [PMID: 16514689]
[http://dx.doi.org/10.1002/asia.200700415] [PMID: 18286564]
[http://dx.doi.org/10.2174/138527211798109204]
[http://dx.doi.org/10.1021/ja805693p] [PMID: 18847268]
[http://dx.doi.org/10.1002/chem.201003694] [PMID: 21590822]
[http://dx.doi.org/10.1021/acs.joc.9b00911] [PMID: 31188599]
[http://dx.doi.org/10.1021/acs.joc.9b01268] [PMID: 31318546]
[http://dx.doi.org/10.1021/acs.joc.8b01245] [PMID: 29956933]
[http://dx.doi.org/10.1021/acs.joc.9b00837] [PMID: 31117570]
[http://dx.doi.org/10.1021/jo401585v] [PMID: 23984761]
[http://dx.doi.org/10.1021/ol502123z] [PMID: 25144620]
[http://dx.doi.org/10.1021/acs.orglett.5b02668] [PMID: 26524623]
[http://dx.doi.org/10.1021/ol400025a] [PMID: 23463941]
[http://dx.doi.org/10.1002/anie.200904779]
[http://dx.doi.org/10.1021/acs.joc.8b01847] [PMID: 30277392]
[http://dx.doi.org/10.1039/C6OB00119J] [PMID: 26978187]
[http://dx.doi.org/10.1021/acs.joc.6b00196] [PMID: 27100356]
[http://dx.doi.org/10.1021/acs.joc.6b00543] [PMID: 27244116]
[http://dx.doi.org/10.1002/ejoc.201300331]
[http://dx.doi.org/10.1002/ejoc.201101086]
[http://dx.doi.org/10.1016/j.tetasy.2010.04.019]
[http://dx.doi.org/10.1016/j.tetasy.2012.03.020]
[http://dx.doi.org/10.2174/1570178615666171226163338]
[http://dx.doi.org/10.1002/chir.22279] [PMID: 24420919]
[http://dx.doi.org/10.1016/j.tetasy.2012.11.009]
[http://dx.doi.org/10.6023/cjoc201706025]
[http://dx.doi.org/10.1016/j.tetlet.2017.10.026]
[http://dx.doi.org/10.1021/ol0701666] [PMID: 17288432]
[http://dx.doi.org/10.1021/ol050431s] [PMID: 15876031]