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

共 30 条

[21] ASYMMETRIC AMPLIFYING PHENOMENA IN ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].

OGUNI, N ;

MATSUDA, Y ;

KANEKO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7877-7878

[22] The asymmetric synthesis of aziridines [J].

Osborn, HMI ;

Sweeney, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1693-1715

[23] NONLINEAR EFFECTS IN ASYMMETRIC-SYNTHESIS - EXAMPLES IN ASYMMETRIC OXIDATIONS AND ALDOLIZATION REACTIONS [J].

PUCHOT, C ;

SAMUEL, O ;

DUNACH, E ;

ZHAO, S ;

AGAMI, C ;

KAGAN, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2353-2357

[24] A novel two-step preparation of enaminoketones by amination of α,β-unsaturated ketones with methoxyamine [J].

Seko, S ;

Tani, N .

TETRAHEDRON LETTERS, 1998, 39 (44) :8117-8120

[25] Chiral Lewis acid catalysis in conjugate additions of O-benzylhydroxylamine to unsaturated amides.: Enantioselective synthesis of β-amino acid precursors [J].

Sibi, MP ;

Shay, JJ ;

Liu, M ;

Jasperse, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6615-6616

[26] Readily available nitrene precursors increase the scope of Evans' asymmetric aziridination of olefins [J].

Sodergren, MJ ;

Alonso, DA ;

Andersson, PG .

TETRAHEDRON-ASYMMETRY, 1997, 8 (21) :3563-3565

[27]

TANNER D, 1994, ANGEW CHEM INT EDIT, V33, P599, DOI 10.1002/anie.199405991

[28] Water vs. desiccant. Improvement of Yb-BINOL complex catalyzed enantioselective epoxidation of enones [J].

Watanabe, S ;

Kobayashi, Y ;

Arai, T ;

Sasai, H ;

Bougauchi, M ;

Shibasaki, M .

TETRAHEDRON LETTERS, 1998, 39 (40) :7353-7356

[29] The first catalytic enantioselective synthesis of cis-epoxyketones from cis-enones [J].

Watanabe, S ;

Arai, T ;

Sasai, H ;

Bougauchi, M ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8090-8091

[30]

WEBER FG, 1985, Z CHEM, V25, P175

← 1 2 3 →