title: Synthesis of 2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-3-((dimethylamino)methyl)camphor organocatalysts.
abstract: In a stereo-divergent synthesis, three novel camphor-derived bifunctional thiourea organocatalysts 7-9 have been prepared in five steps starting from (+)-camphor. In addition, borneol-derived bifunctional thiourea organocatalysts 19/19' have been prepared in three steps from (1S)-(+)-camphorquinone. Novel organocatalysts 7-9, 19/19' have been evaluated in a model reaction of Michael addition of dimethyl malonate to trans-β-nitrostyrene with low to moderate enantioselectivities (20%-60% ee). Configuration of all novel compounds has been meticulously determined using nuclear magnetic resonance (NMR) techniques.
authors.affiliation: Organic chemistry, University of Ljubljana, Faculty of Chemistry and Chemical Technology, Ljubljana, Slovenia. uros.groselj@fkkt.uni-lj.si
authors.forename: Uroš
authors.initials: U
authors.lastname: Grošelj
authors.forename: Sebastjan
authors.initials: S
authors.lastname: Ričko
authors.forename: Jurij
authors.initials: J
authors.lastname: Svete
authors.forename: Branko
authors.initials: B
authors.lastname: Stanovnik