Metal-containing ionic liquids as efficient catalysts for hydroxymethylation in water

被引：64

作者：

Bica, Katharina ^{[1
]}

Gaertner, Peter ^{[1
]}

机构：

[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 20期

关键词：

ionic liquids; iron; water chemistry; hydroxymethylation; lactones;

D O I：

10.1002/ejoc.200800323

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iron-containing ionic liquid butylmethylimidazolium tetrachloroferrate (bmim-FeCl4) proved to be an efficient and recyclable catalyst for the hydroxymethylation of beta-keto esters using aqueous formaldehyde and a low catalyst loading of up to 0.1 mol-% without co-solvents or additional surfactants. An useful and high-yielding approach to hydroxymethylated keto esters as well as to 3-disubstitued butyrolactones via tandem hydroxymethylation-lactonization could thus be established. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：3453 / 3456

页数：4

共 30 条

[1] A chemo-enzymatic elaboration of a quarternary chiral center: an alternative approach to the side chain of furaquinocin D [J].

Akeboshi, T ;

Ohtsuka, Y ;

Sugai, T ;

Ohta, H .

TETRAHEDRON, 1998, 54 (26) :7387-7394

[2]

[Anonymous], 2004, MODERN ALDOL REACTIO

[3] An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides [J].

Bica, K ;

Gaertner, P .

ORGANIC LETTERS, 2006, 8 (04) :733-735

[4] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[5] Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes [J].

Casas, J ;

Sundén, H ;

Córdova, A .

TETRAHEDRON LETTERS, 2004, 45 (32) :6117-6119

[6] ANGULAR HYDROXYMETHYLATION OF FUNCTIONALIZED DECALIN SYSTEMS [J].

CHAN, TH ;

SCHWERDTFEGER, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3294-3298

[7]

CHENG Y, 2004, Patent No. 167096

[8]

DUPONT CS, 2003, ORG SYNTH, V79, P236

[9]

DYSON P, 2003, CHEM ALTERNATIVE REA

[10] Catalytic asymmetric aldol reactions of enolizable carbon pronucleophiles with formaldehyde and ethyl glyoxylate [J].

Fukuchi, Isao ;

Hamashima, Yoshitaka ;

Sodeoka, Mikiko .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) :509-512

← 1 2 3 →