83487-79-0Relevant academic research and scientific papers
REGIO- AND STEREOSELECTIVITY IN THE AMINATION OF CYCLOHEXANONE ENAMINES
Fioravanti, Stefania,Pellacani, Lucio,Tardella, Paolo A.
, p. 41 - 44 (2007/10/03)
The portionwise addition of ethyl N-carbamate (TsONHCO2Et) in the presence of solid caesium carbonate enables the regioselective amination of 1-(1-cyclohexenyl)pyrroloidine, to give mainly the C-amination product 2-cyclohexanone in 38percent yield.In the absence of base, the batchwise addition of TsONHCO2Et exlusively give the N-amination product (48percent).With ethyl N-carbamate (NsONHCO2Et) as the aminating agent, the regioselectivity is depending on the reaction conditions.The optically active enamine (S)-(-)-1-(1-cyclohexenyl)-2-(methoxymethyl)pyrrolidine reacts with NsONHCO2Et yielding a product whose stereoselectivity depends on the reaction conditions.In the presence of CaO, the major enantiomer has a configuration (S) opposite that of the major enantiomer obtained in the presence of Et3N.Amination of the same enamine by another electrophile, bis(tert-butoxycarbonyl)diazene , give 2-cyclohexanone in good yield (66percent).The configuration of the major enantiomer was determined by chemical correlation.
