ASYMMETRIC FORMATION OF C-N BONDS IN CHIRAL ENOL ETHERS

被引：19
作者：
FIORAVANTI, S
LORETO, MA
PELLACANI, L
TARDELLA, PA
机构：
[1] Dipartimento di Chimica, Università La Sapienza, I-00185 Roma
来源：
TETRAHEDRON | 1991年 / 47卷 / 30期
关键词：
DIASTEREOSELECTIVE AZIRIDINATION; CHIRAL ALPHA-AMINO KETONES; NITRENE;
D O I：
10.1016/S0040-4020(01)86538-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 alpha-amino ketone 4. Other chiral auxiliaries does not allow isolation of intermediate aziridines and the alpha-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 alpha-amino ketone with prevailing opposite configuration at the new formed chiral centre.
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收藏
页码：5877 / 5882
页数：6
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