1280655-40-4Relevant academic research and scientific papers
Large-scale Mannich-type reactions of (SS)-N-tert- butanesulfinyl-(3,3,3)-trifluoroacetaldimine with C-nucleophiles
Xie, Chen,Mei, Haibo,Wu, Lingmin,Han, Jianlin,Soloshonok, Vadim A.,Pan, Yi
, p. 67 - 75 (2014)
Here we describe the first attempts to scale up five addition reactions between (SS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine 6 with C-nucleophiles derived from ketones (two examples), glycine Schiff base and heterocycles (two examples). In all cases studied, the observed stereochemical outcome of the scaled up (5.0-25.0 mmol) reactions was lower as compared with the original 0.5 mmol scale. However, the observed worsening of yields and diastereoselectivity was not identical and depended on the reaction conditions and reaction mechanisms. In general, scaling up of the reactions conducted at ambient temperatures presented no problems while the low-temperature (-78 °C) processes would require special equipment to provide strict maintenance of the reaction temperature to obtain the desirable outcome. Importantly, using procedures described here, series of biologically relevant compounds containing 2,2,2-trifluoro-1-(amino)ethyl [CF3CH(NH2)-] pharmacophore unit can be prepared in enantiomerically pure form on up to 5 g scale, allowing their systematic biological studies.
Ni-catalyzed asymmetric decarboxylative Mannich reaction for the synthesis of β-trifluoromethyl-β-amino ketones
Qian, Ping,Dai, Yanling,Mei, Haibo,Soloshonok,Han, Jianlin,Pan, Yi
, p. 26811 - 26814 (2015/03/30)
A new Ni-catalyzed asymmetric decarboxylative Mannich reaction between (Ss)-N-t-butylsulfinyl-3,3,3-trifluoro-acetaldimine and β-keto-acids was developed, which was carried out at room temperature affording β-trifluoromethyl-β-amino ketones with excellent yields and diastereoselectivities.
A facile process for the asymmetric synthesis of β-trifluoromethylated β-amino ketones via addition of ketone enolates to sulfinylimine
Mei, Haibo,Xiong, Yiwen,Han, Jianlin,Pan, Yi
, p. 1402 - 1406 (2011/04/16)
An efficient method for the asymmetric synthesis of β- trifluoromethylated β-amino ketones via addition of ketone-derivative enolates to trifluoromethylated sulfinylimine has been developed, with good chemical yields and excellent diastereoselectivities.
