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Synthesis and catalyst performance of 2,3‐ (types B and C) and 2,8‐disubstituted (type D) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type B has, so far, not been realized, while catalysts of type C, i.e., the 2,3‐exo‐ and the 2‐endo‐3‐exo‐thiourea catalysts, were prepared in six steps starting from (+)‐camphor. The catalysts of type D were prepared from (+)‐camphor...
A simple and straightforward four‐step synthesis of novel diastereomeric L‐phenylalanine‐derived pyrazolidin‐3‐ones is described. The absolute configuration of the novel C(5) stereogenic centre has been unambiguously determined by single crystal X‐ray analysis and via chemical interconversions. A series of novel thiourea derived pyrazolidinones have been prepared and tested as potential organocatalysts...
Two novel 4‐substituted camphidine derivatives 10a,b have been prepared from (+)‐camphor (1) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b, formed as a side product during the hydrogenation of arylidene ketone 3b, under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12. (1S)‐(+)‐Camphorquinone (13...
In a stereo‐divergent synthesis, three novel camphor‐derived bifunctional thiourea organocatalysts 7, 8, 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, 8, 9, 19/19’ have been evaluated in a model reaction of Michael addition...
Nine novel (+)‐camphor‐derived thioureas have been prepared. 3‐((Dimethylamino)methylene)camphor (2) served as the common precursor for the preparation of both, 2‐thiourea 15, 16, 17, 18, 19, 20 and 3‐thiourea functionalized camphor derivatives 6, 7/7', respectively. Starting from 2, the latter were prepared in two or three steps whereas the former in five steps, respectively. Configuration of all...
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