1427296-12-5Relevant articles and documents
Asymmetric Aza-Diels-Alder Reactions of in Situ Generated β,β-Disubstituted α,β-Unsaturated N-H Ketimines Catalyzed by Chiral Phosphoric Acids
He, Shunlong,Gu, Huanchao,He, Yu-Peng,Yang, Xiaoyu
, p. 5633 - 5639 (2020)
A novel asymmetric synthesis of dihydropyridinones with vicinal quaternary stereocenters has been realized by asymmetric aza-Diels-Alder reactions of 3-amido allylic alcohols with oxazolones enabled by chiral phosphoric acid catalysis. A series of aryl/alkyl- and alkyl/alkyl-disubstituted 3-amido allylic tertiary alcohols and 4-substituted oxazolones could be well tolerated in these reactions, producing dihydropyridinones with excellent diastereoselectivities and high enantioselectivities. Mechanistic study and control experiments were performed to shed light on the reaction mechanism, in which a configurationally defined β,β-disubstituted α,β-unsaturated N-H ketimine was proposed as the key intermediate.
Copper-catalyzed aldol-type addition of ketones to aromatic nitriles: A simple approach to enaminone synthesis
Yu, Xiaoqiang,Wang, Longxiang,Feng, Xiujuan,Bao, Ming,Yamamoto, Yoshinori
supporting information, p. 2885 - 2887 (2013/04/24)
An efficient method for the synthesis of enaminones is described. The aldol-type addition of ketones to aromatic nitriles proceeded smoothly in the presence of a simple copper catalyst system (CuI-2,2′-bipyridine-NaO tBu) in N,N-dimethylformamide. Enaminones in satisfactory to excellent yields were produced using this technique. The Royal Society of Chemistry 2013.