Chiral thiourea-phosphine organocatalysts in the asymmetric Aza-Morita-Baylis-Hillman reaction

被引：119

作者：

Shi, Yong-Ling ^{[1
]}

Shi, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 13期

关键词：

asymmetric catalysis; Morita-Baylis-Hillman reaction; NMR spectroscopy; organic catalysis; thiourea-phosphine organocatalysts;

D O I：

10.1002/adsc.200700155

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new kind of bifunctional (thio)ureapbosphine catalyst was synthesized and applied to the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone, phenyl vinyl ketone, ethyl vinyl ketone or acrolein. Moderate to excellent ee and yields of the products were obtained under mild reaction conditions.

引用

页码：2129 / 2135

页数：7

共 39 条

[1] Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis [J].

Aggarwal, VK ;

Fulford, SY ;

Lloyd-Jones, GC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1706-1708

[2] Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].

Barrett, AGM ;

Cook, AS ;

Kamimura, A .

CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534

[3] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[4] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[5] Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts [J].

Berkessel, Albrecht ;

Roland, Katrin ;

Neudoerfl, Jorg M. .

ORGANIC LETTERS, 2006, 8 (19) :4195-4198

[6] A staudinger approach towards binol-derived MAP-type bidentate PN ligands [J].

Botman, PNM ;

David, O ;

Amore, A ;

Dinkelaar, J ;

Vlaar, MT ;

Goubitz, K ;

Fraanje, J ;

Schenk, H ;

Hiemstra, I ;

van Maarseveen, JH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3471-3473

[7] Bifunctional activation and racemization in the catalytic asymmetric aza-Baylis-Hillman reaction [J].

Buskens, P ;

Klankermayer, J ;

Leitner, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :16762-16763

[8]

Ciganek E., 1997, ORG REACTIONS, V51, P201

[9] Organocatalysis mediated by (thio)urea derivatives [J].

Connon, Stephen J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427

[10]

Dean J. A., 1998, LANGES HDB CHEM

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