Enantioselective N‐Heterocyclic Carbene Catalysis by the Umpolung of α,β‐Unsaturated Ketones |
| |
Authors: | Yuji Nakano Prof Dr David W Lupton |
| |
Institution: | School of Chemistry, Monash University, Clayton, Victoria, Australia |
| |
Abstract: | N‐Heterocyclic carbene‐catalyzed formation of β‐anionic intermediates from enones has been employed in the enantioselective synthesis of 2‐aryl propionates. The reaction was achievable using a homochiral 4‐MeOC6H4 morpholinone catalyst allowing the first example of enantioselective catalysis by umpolung of α,β‐unsaturated ketones. The reaction is high yielding, and shows robustness with reasonable generality. A mechanism is proposed in which the enantiodetermining protonation is achieved using either hexafluoroisopropanol or the formed naphthol product. |
| |
Keywords: | 1 4-addition 2-aryl propionates enantioselective catalysis N-heterocyclic carbenes β -azolium ylides |
|
|