Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes

被引：49

作者：

Sugihara, H ^{[1
]}

Daikai, K ^{[1
]}

Jin, XL ^{[1
]}

Furuno, H ^{[1
]}

Inanaga, J ^{[1
]}

机构：

[1] Kyushu Univ, Inst Fundamental Res Organ Chem, IFOC, Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 15期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(02)00361-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active N-unsubstituted alpha-keto aziridines 2 were synthesized from conjugated enones I via the Sc[(R)-BNP](3)-catalyzed enantioselective Michael addition of O-methylhydroxylamine followed by the La(O-l-Pr)(3)-catalyzed ring closure of the corresponding beta-methoxyamino ketones 3. A remarkably high asymmetric amplification was observed during the Michael addition, and notable kinetic resolution was also realized during the ring closure reaction when a La(O-i-Pr)(3)-(R)-BINOL catalyst system was employed. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2735 / 2739

页数：5

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