[AlCl₃ + 2THF]:  A New and Efficient Catalytic System for Diels−Alder Cycloaddition of α,β-Unsaturated Carbonyl Compounds under Solvent-Free Conditions

Abstract

[AlCl(3) + 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. [reaction: see text]

Addition Reactions: Cycloaddition

“…102 [AlCl 3 + 2THF] is a new and effiee cient catalytic system for the Diels-Alder cycloaddition of α,β-unsaturated carbonyl compounds with dienes under solvent-free conditions. 103 Dendritic copper(II) triflate catalysts with a 2,2 -bipyridine core (92) …”

“…Triplet-sensitized irradiation of these bridged bicyclooctenones produced bicyclo[3.3.0]octanoids, whereas direct irradiation yielded bicyclo[4.2.0]octanes. 135 Cinchona alkaloid derivatives catalysed the enantioselective 4 + 2-cycloaddition of o-quinones with ketene enolates to produce chiral o-quinone cycloadducts in high ee ee (103) and good to excellent yields. The cycloadducts can be readily converted into optically active α-hydroxy esters in the presence of ceric ammonium nitrate.…”

Diastereoselective Three‐Step Route to o‐(6‐Nitrocyclohex‐3‐en‐1‐yl)phenol and Tetrahydro‐6H‐benzo[c]chromen‐6‐ol Derivatives from Salicylaldehydes

“…[1] Our research group has been committed to the development of efficient synthetic protocols that mainly use either water as reaction medium [2] or solvent-free conditions (SolFC). [3] In particular, we have paid attention to the preparation of valuable heterocyclic moieties such as 1H-triazoles and 1H-tetrazoles, [4] dihydrodibenzo [b,d]furans, [5] biphenyl-2-carbonitrile derivatives, [6] benzo[e]1,4-oxathiepin-5-ones, [7] quinoxaliniuim, and thiazolopyridinium salts.…”

“…[6][7][8][9] We have also shown that running the reactions under solventfree conditions when a solid supported catalyst is used is a convenient approach because it allows the environmental cost to be minimized and a beneficial effect on the chemical [ …”

Diels-Alder Cycloaddition of Cyclopentadiene with Ethylacrylate Catalyzed by Mesoporous Al-MCM-48 and Al-MCM-41 Catalysts

“…[4][5][6] A few solid acid catalysts have been also found to be useful in the DA reaction. [7][8][9][10][11] In general, the heterogeneous catalysts exhibit several advantages compared with the homogeneous catalysts due to their importance in practical productions of chemicals from the viewpoints of the so-called "zeroemission" or "green" chemistry and ease of separation from the reaction mixture.…”