Acceleration of the DABCO-promoted Baylis-Hillman reaction using a recoverable H-bonding organocatalyst

被引：133

作者：

Maher, DJ ^{[1
]}

Connon, SJ ^{[1
]}

机构：

[1] Univ Dublin Trinity Coll, Dept Chem, Dublin 2, Ireland

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 06期

关键词：

catalysis; Michael addition; amine; urea; H-bonding;

D O I：

10.1016/j.tetlet.2003.11.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been shown that catalytic amounts (20-40 mol%) of bis-aryl (thio)ureas greatly accelerate the DABCO-promoted Baylis-Hillman reaction between a range of aromatic aldehydes and methyl acrylate in the absence of solvent. These robust organocatalysts are superior mole per mole promoters of the reaction than either methanol or water and are recoverable in high yield after the reaction by column chromatography. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1301 / 1305

页数：5

共 55 条

[1] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope [J].

Aggarwal, VK ;

Emme, I ;

Fulford, SY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :692-700

[2] Unexpected side reactions of imidazolium-based ionic liquids in the base-catalysed Baylis-Hillman reaction [J].

Aggarwal, VK ;

Emme, I ;

Mereu, A .

CHEMICAL COMMUNICATIONS, 2002, (15) :1612-1613

[3] Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated [J].

Aggarwal, VK ;

Dean, DK ;

Mereu, A ;

Williams, R .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :510-514

[4] Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications [J].

Aggarwal, VK ;

Mereu, A .

CHEMICAL COMMUNICATIONS, 1999, (22) :2311-2312

[5] First-examples of metal and ligand accelerated catalysis of the Baylis-Hillman reaction [J].

Aggarwal, VK ;

Tarver, GJ ;

McCague, R .

CHEMICAL COMMUNICATIONS, 1996, (24) :2713-2714

[6] Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].

Aggarwal, VK ;

Mereu, A ;

Tarver, GJ ;

McCague, R .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189

[7] RATE ENHANCEMENT EFFECTS IN THE DABCO CATALYZED SYNTHESIS OF HYDROXYALKENOATE ESTERS [J].

AMEER, F ;

DREWES, SE ;

FREESE, S ;

KAYE, PT .

SYNTHETIC COMMUNICATIONS, 1988, 18 (05) :495-500

[8] ACCELERATION IN WATER OF THE BAYLIS-HILLMAN REACTION [J].

AUGE, J ;

LUBIN, N ;

LUBINEAU, A .

TETRAHEDRON LETTERS, 1994, 35 (43) :7947-7948

[9] STEREOSELECTIVE EPOXIDATION OF HYDROXYENONES - THE SYNTHESIS OF THE SIDE-CHAIN OF CLEROCIDIN [J].

BAILEY, M ;

MARKO, IE ;

OLLIS, WD ;

RASMUSSEN, PR .

TETRAHEDRON LETTERS, 1990, 31 (31) :4509-4512

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

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

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

← 1 2 3 4 5 6 →