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

来源：

TETRAHEDRON | 1997年 / 53卷 / 13期

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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收藏

页码：4779 / 4786

页数：8

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