Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals

被引:10
作者
Fioravanti, S
Luna, G
Pellacani, L
Tardella, PA
机构
[1] Dipartimento di Chimica, Università La Sapienza, I-00185 Roma
关键词
D O I
10.1016/S0040-4020(97)00161-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically active cyclohex-3-en-1-one ketals by photolysis of N(3)CO(2)Et or N3C(OEt)NMs or by CaO induced alpha-elimination of NsONHCO(2)Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-beta-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier Science Ltd.
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页码:4779 / 4786
页数:8
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