Tetrahedron p. 5877 - 5882 (1991)
Update date:2022-09-26
Topics:
Fioravanti, Stefania
Antonietta Loreto
Pellacani, Lucio
Tardella, Paolo A.
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.
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Doi:10.1021/bm300103u
(2012)Doi:10.1039/c39910001154
(1991)Doi:10.1021/jo00053a015
(1993)Doi:10.1021/ja00024a081
(1991)Doi:10.1248/cpb.39.1857
(1991)Doi:10.1016/S0040-4039(00)79870-4
(1991)