[AlCl3+2THF]:: A new and efficient catalytic system for Diels-Alder cycloaddition of α,β-unsaturated carbonyl compounds under solvent-free conditions

被引：56

作者：

Fringuelli, Francesco ^{[1
]}

Girotti, Rugiada ^{[1
]}

Pizzo, Ferdinando ^{[1
]}

Vaccaro, Luigi ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim, CEMIN, I-06123 Perugia, Italy

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

关键词：

D O I：

10.1021/ol060569q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[AlCl3+2THF] is a new catalytic system for the Diels-Alder cycloaddition under SFC and air atmosphere. By using equimolar amounts of reactants, this catalyst prevents the polymerization of the diene and allows the corresponding adducts to be isolated with high regio- and stereocontrol and in excellent yields.

引用

页码：2487 / 2489

页数：3

共 29 条

[1] Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3+2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions [J].

Amantini, D ;

Fringuelli, F ;

Piermatti, O ;

Pizzo, F ;

Zunino, E ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6526-6529

[2] 3-nitrocoumarins as dienophiles in the Diels-Alder reaction in water. An approach to the synthesis of nitrotetrahydrobenzo[c]chromenones and dihydrodibenzo[b,d]furans [J].

Amantini, D ;

Fringuelli, F ;

Piermatti, O ;

Pizzo, F ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9263-9268

[3]

Anastas P. T., 1998, GREEN CHEM THEORY PR

[4] MODELS FOR THE USE OF ALPHA-AMINO-ACIDS AS CHIRAL AUXILIARIES IN ASYMMETRIC DIELS-ALDER REACTIONS [J].

BUENO, MP ;

CATIVIELA, CA ;

MAYORAL, JA ;

AVENOZA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6551-6555

[5] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].

Cave, GWV ;

Raston, CL ;

Scott, JL .

CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169

[6] SPECTROSCOPIC INVESTIGATION OF ALUMINUM TRIHALIDE-TETRAHYDROFURAN COMPLEXES .2. SOLUTIONS OF ALUMINUM-CHLORIDE OR BROMIDE IN TETRAHYDROFURAN AND IN TETRAHYDROFURAN-DICHLOROMETHANE [J].

DEROUAULT, J ;

GRANGER, P ;

FOREL, MT .

INORGANIC CHEMISTRY, 1977, 16 (12) :3214-3218

[7]

ELIAS GH, 2005, INTRO POLYM SCI, P73

[8] DIELS-ALDER REACTIONS OF CYCLOALKENONES .16. ENDO DIASTEREOSELECTIVITY OF SOME CYCLOALKENONES IN REACTIONS WITH 1,3-CYCLOHEXADIENE [J].

FRINGUELLI, F ;

GUO, M ;

MINUTI, L ;

PIZZO, F ;

TATICCHI, A ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :710-712

[9] InCl3-catalyzed regio- and stereloselective thiolysis of α,β-epoxycarboxylic acids in water [J].

Fringuelli, F ;

Pizzo, F ;

Tortoioli, S ;

Vaccaro, L .

ORGANIC LETTERS, 2005, 7 (20) :4411-4414

[10] One-pot synthesis of benzo[e]1,4-oxathiepin-5-ones under solvent-free condition via self-promoted thiolysis of 1,2-epoxides [J].

Fringuelli, F ;

Pizzo, F ;

Tortoioli, S ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8780-8785

← 1 2 3 →