1599440-76-2Relevant academic research and scientific papers
Nitrogen nucleophiles in au-catalyzed dehydrative cyclization reactions
Ketcham, John M.,Cardoso, Flavio S. P.,Biannic, Berenger,Piras, Henri,Aponick, Aaron
, p. 923 - 931 (2013)
Mild conditions for the gold-catalyzed dehydrative cyclization of carbamate-protected azaallylic alcohols to form saturated nitrogen heterocycles are reported. The cyclization reactions are high-yielding, operationally easy to perform, and provide heterocycles with a synthetically useful vinyl group, strategically located on the ring system, which can facilitate further transformations for target oriented synthesis. It is also demonstrated through chirality transfer experiments that the mechanism can be either cationic in nature or a Au-catalyzed addition/elimination sequence. The diverging mechanistic scenario is dependent on the nature of the substituents on the allylic alcohol and necessitates judicious substrate design.
