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Issue 12, 2013
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Synthesis and catalytic activity of fluorous chiral primary amine-thioureas

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Abstract

Three enantiopure fluorous thioureas featuring a free –NH2 group were synthesized by direct addition of aromatic isothiocyanates bearing a single n-C8F17 substituent in the ortho, meta and para position, respectively, to enantiopure (1R,2R)-1,2-diaminocyclohexane. The catalytic behavior of these bifunctional molecules was assessed in representative Michael-type reactions. The three fluorous thioureas performed similarly in all the reactions tested, thus showing that the position of the fluorous ponytail does not have a major influence on the catalytic behavior of this class of compounds. In particular, excellent enantioselectivities (up to 99% ee) and yields (up to 98%) were obtained for the addition of aliphatic aldehydes to maleimides to give α-substituted succinimides. Recyclability of these primary amine-based thioureas was found to be limited by the concurrent formation of imine-derivatives during the catalytic process, leading to a structural modification of the organic catalyst.

Graphical abstract: Synthesis and catalytic activity of fluorous chiral primary amine-thioureas

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Supplementary files

Article information


Submitted
22 Jul 2013
Accepted
24 Sep 2013
First published
25 Sep 2013

New J. Chem., 2013,37, 4140-4147
Article type
Paper

Synthesis and catalytic activity of fluorous chiral primary amine-thioureas

S. Orlandi, G. Pozzi, M. Ghisetti and M. Benaglia, New J. Chem., 2013, 37, 4140
DOI: 10.1039/C3NJ00807J

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