19134-43-1Relevant academic research and scientific papers
Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: A one-step synthesis of plavix
Evans, Ryan W.,Zbieg, Jason R.,Zhu, Shaolin,Li, Wei,Macmillan, David W. C.
, p. 16074 - 16077 (2013)
The direct α-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful α-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated α-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the α-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.
