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

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[2] Synthesis and applications of C2-symmetric guanidine bases [J].

Allingham, MT ;

Howard-Jones, A ;

Murphy, PJ ;

Thomas, DA ;

Caulkett, PWR .

TETRAHEDRON LETTERS, 2003, 44 (48) :8677-8680

[3] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].

Andrey, O ;

Alexakis, A ;

Bernardinelli, G .

ORGANIC LETTERS, 2003, 5 (14) :2559-2561

[4]

[Anonymous], 2005, ANGEW CHEM, V117, P817

[5]

Bako P, 1997, SYNLETT, P291

[6] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].

Barnes, DM ;

Ji, JG ;

Fickes, MG ;

Fitzgerald, MA ;

King, SA ;

Morton, HE ;

Plagge, FA ;

Preskill, M ;

Wagaw, SH ;

Wittenberger, SJ ;

Zhang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105

[7] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].

Berkessel, A ;

Cleemann, F ;

Mukherjee, S ;

Müller, TN ;

Lex, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811

[8]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[9] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[10] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Barbas, CF .

TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444

← 1 2 3 4 5 6 7 8 9 10 →