Synthesis of 2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-3-((dimethylamino)methyl)camphor organocatalysts
Grošelj, U; Ričko, S; Svete, J; Stanovnik, B
| HERO ID | 4923528 |
|---|---|
| In Press | No |
| Year | 2012 |
| Title | Synthesis of 2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-3-((dimethylamino)methyl)camphor organocatalysts |
| Authors | Grošelj, U; Ričko, S; Svete, J; Stanovnik, B |
| Journal | Chirality |
| Volume | 24 |
| Issue | 5 |
| Page Numbers | 412-419 |
| 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. |
| Doi | 10.1002/chir.22035 |
| Pmid | 22514057 |
| Wosid | WOS:000303237200009 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |