113618-36-3Relevant academic research and scientific papers
Asymmetric formation of C - N bonds in chiral enol ethers
Fioravanti, Stefania,Antonietta Loreto,Pellacani, Lucio,Tardella, Paolo A.
, p. 5877 - 5882 (2007/10/02)
Attack of EtO2CN on an enol ether carrying (S,S)-hydrobenzoin as chiral auxiliary gives diastereoselective aziridination with diastereomeric excess> 95%. Easy subsequent hydrolysis gives partially racemised α-amino ketone 4. Other chiral auxiliaries does not allow isolation of intermediate aziridines and the α-amino ketone is isolated with a 75:25 enantiomeric ratio. The thermolysis of EtO2CN3 in most of the same enol ethers gives the acetals of the α-amino ketone with prevailing opposite configuration at the new formed chiral centre.
