Michael addition-electrophilic quenching chemistry of maleimides using dialkylzinc reagents

被引：10

作者：

Dardennes, Emmanuel ^{[1
]}

Labano, Stefania ^{[1
]}

Simpkins, Nigel S. ^{[1
]}

Wilson, Claire ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 36期

基金：

英国工程与自然科学研究理事会;

关键词：

imide; Michael addition; dialkylzinc; phosphoramidite; asymmetric catalysis;

D O I：

10.1016/j.tetlet.2007.06.155

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Michael addition-electrophilic quench reactions of N-alkyl maleimides are possible using dialkylzincs in combination with a copper catalyst and a phosphoramidite ligand. Up to 55% ee has been achieved for one example (E = H) using a chiral ligand. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6380 / 6383

页数：4

共 27 条

[1]

Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].

Arnold, LA ;

Imbos, R ;

Mandoli, A ;

de Vries, AHM ;

Naasz, R ;

Feringa, BL .

TETRAHEDRON, 2000, 56 (18) :2865-2878

[2]

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

[3]

SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 3-ETHYL AND 3-NORMAL-PROPYLPYRROLIDINE [J].

BETTONI, G ;

CELLUCCI, C ;

BERARDI, F .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (03) :603-605

[4]

Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes [J].

Brown, MK ;

Degrado, SJ ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5306-5310

[5]

Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].

Feringa, BL .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353

[6]

ANDRIMID, A NEW PEPTIDE ANTIBIOTIC PRODUCED BY AN INTRACELLULAR BACTERIAL SYMBIONT ISOLATED FROM A BROWN PLANTHOPPER [J].

FREDENHAGEN, A ;

TAMURA, SY ;

KENNY, PTM ;

KOMURA, H ;

NAYA, Y ;

NAKANISHI, K ;

NISHIYAMA, K ;

SUGIURA, M ;

KITA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4409-4411

[7]

Catalytic asymmetric tandem transformations triggered by conjugate additions [J].

Guo, HC ;

Ma, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (03) :354-366

[8]

Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].

Hayashi, T ;

Yamasaki, K .

CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844

[9]

Theoretical study on the polymerization mechanism of substituted maleimides by using a chiral catalyst with Zn2+ [J].

Hori, K ;

Yoshimura, K ;

Ohno, H ;

Onimura, K ;

Oishi, T .

TETRAHEDRON, 2003, 59 (33) :6301-6309

[10]

Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions [J].

Howell, Gareth P. ;

Fletcher, Stephen P. ;

Geurts, Koen ;

ter Horst, Bjorn ;

Feringa, Ben L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14977-14985

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