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- W2949919371 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." @default.
- W2949919371 created "2019-06-27" @default.
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- W2949919371 date "2014-05-15" @default.
- W2949919371 modified "2023-09-23" @default.
- W2949919371 title "ChemInform Abstract: Synthesis and Catalytic Activity of Fluorous Chiral Primary Amine-Thioureas." @default.
- W2949919371 cites W2131216566 @default.
- W2949919371 doi "https://doi.org/10.1002/chin.201422024" @default.
- W2949919371 hasPublicationYear "2014" @default.
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