Rate Acceleration of Triethylamine-Mediated Guanidine-Catalyzed Enantioselective Michael Reaction

被引：71

作者：

Jiang, Zhiyong ^{[1
]}

Ye, Weiping ^{[1
]}

Yang, Yuanyong ^{[1
]}

Tan, Choon-Hong ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 14-15期

关键词：

asymmetric catalysis; chiral bicyclic guanidines; Michael addition; organic catalysis; triethylamine (Et3N);

D O I：

10.1002/adsc.200800423

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A chiral bicyclic guanidine was found to be an excellent catalyst for enantioselective Michael reactions. It was observed that additives such as non-chiral amines could accelerate the rate of reaction. When triethylamine (Et3N) was as used as the solvent, the reaction rate can be increased up to 1000 times without compromising the enantioselectivity. Michael acceptors such as 2-cyclopenten-1-one 2 and N-alkylmaleimides were investigated, with various commercially available Michael donors such as dialkyl malonates and benzoylactetates. Michael adducts were obtained in excellent enantiomeric excesses (up to 96%) and yields (up to 99%).

引用

页码：2345 / 2351

页数：7

共 51 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] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].

Andrey, O ;

Alexakis, A ;

Tomassini, A ;

Bernardinelli, G .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168

[3] A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].

Arai, T ;

Sasai, H ;

Aoe, K ;

Okamura, K ;

Date, T ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106

[4]

ARAI T, 1996, ANGEW CHEM, V108, P103

[5] Conjugate addition of nitroalkanes to N-substituted maleimides.: Synthesis of 3-alkylsuccinimides and pyrrolidines [J].

Ballini, R ;

Bosica, G ;

Cioci, G ;

Fiorini, D ;

Petrini, M .

TETRAHEDRON, 2003, 59 (20) :3603-3608

[6]

Bartoli G, 2006, ANGEW CHEM, V118, P5088, DOI DOI 10.1002/ange.200600370

[7] Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides [J].

Bartoli, Giuseppe ;

Bosco, Marcella ;

Carlone, Armando ;

Cavalli, Andrea ;

Locatelli, Manuela ;

Mazzanti, Andrea ;

Ricci, Paolo ;

Sambri, Letizia ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4966-4970

[8]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P9

[9] Solvent and temperature effects on diastereofacial selectivity:: Amines as co-solvents in n-butyllithium addition to α-chiral aldehydes [J].

Cainelli, G ;

Giacomini, D ;

Galletti, P ;

Quintavalla, A .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) :1993-2000

[10] ENANTIOSPECIFIC SYNTHESIS OF A RIGID, C-2 SYMMETRIC, CHIRAL GUANIDINE BY A NEW AND DIRECT METHOD [J].

COREY, EJ ;

OHTANI, M .

TETRAHEDRON LETTERS, 1989, 30 (39) :5227-5230

← 1 2 3 4 5 6 →