Enantioselective Michael addition to α,β-unsaturated imides catalyzed by a bifunctional organocatalyst

被引：267

作者：

Hoashi, Y ^{[1
]}

Okino, T ^{[1
]}

Takemoto, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 26期

关键词：

imides; Michael addition; nitriles; organocatalysis; thiourea;

D O I：

10.1002/anie.200500459

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) High enantioselectivities (up to 94 % ee) were attained in the Michael addition of a variety of α,β-unsaturated imides 1 and malononitrile (2) catalyzed by bifunctional thiourea 4. The pyrrolidinone moiety of 1 plays a key role in the reaction. The reaction provides access to a variety of Michael adducts 3 (see scheme; R = aryl and alkyl groups). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4032 / 4035

页数：4

共 99 条

[31] Organocatalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated enones using novel imidazoline catalysts [J].

Halland, N ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8331-8338

[32]

Halland N., 2003, ANGEW CHEM, V115, P685, DOI DOI 10.1021/OL050431S

[33]

Halland N., 2003, ANGEW CHEM, V115, P5105

[34] Immobilization and reuse of Pd complexes in ionic liquid:: Efficient catalytic asymmetric fluorination and Michael reactions with β-ketoesters [J].

Hamashima, Y ;

Takano, H ;

Hotta, D ;

Sodeoka, M .

ORGANIC LETTERS, 2003, 5 (18) :3225-3228

[35] Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].

Hamashima, Y ;

Hotta, D ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241

[36] Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones [J].

Hanessian, S ;

Pham, V .

ORGANIC LETTERS, 2000, 2 (19) :2975-2978

[37] MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST [J].

HUBERT, AJ .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :1984-&

[38] Enantioselective Michael addition reactions of malononitrile catalyzed by chiral Lewis acid and achiral amine catalysts [J].

Itoh, K ;

Oderaotoshi, Y ;

Kanemasa, S .

TETRAHEDRON-ASYMMETRY, 2003, 14 (06) :635-639

[39] Enantioselective Michael additions of nitromethane by a catalytic double activation method using chiral Lewis acid and achiral amine catalysts [J].

Itoh, K ;

Kanemasa, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13394-13395

[40] Amino acids and peptides as asymmetric organocatalysts [J].

Jarvo, ER ;

Miller, SJ .

TETRAHEDRON, 2002, 58 (13) :2481-2495

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