A novel and convenient approach, the domino retro Diels-Alder/Diels-Alder reaction sequence for highly stereo- and regioselective synthesis of various bicyclo[2.2.2]octenone and bicyclo[2.2.2]octadienone derivatives is presented. Thus, the masked o-benzoquinones (MOBs) 2a-e generated by the pyrolysis of the respective dimers 3a-e participated in this novel synthetic strategy with a variety of o...

The first total synthesis of (+)-cytosporolide A was achieved by a biomimetic hetero-Diels-Alder reaction of (-)-fuscoatrol A with o-quinone methide generated from (+)-CJ-12,373. The dienophile, highly oxygenated caryophyllene sesquiterpenoid (-)-fuscoatrol A, was synthesized from the synthetic intermediate in our previous total synthesis of (+)-pestalotiopsin A. The o-quinone methide precursor...

Two catalysts, Me(2)AlNTf(2) and MeAl(NTf(2))(2), derived from the mixing of trimethylaluminum with triflimide, proved to be highly effective catalysts in hindered Diels-Alder reactions, generating the desired Diels-Alder cycloadducts from both hindered 2-silyloxydienes and hindered dienophiles. Thus reaction of 1 with 2 afforded the hindered cycloadduct 4 in excellent yield in 0.5-1.5 h at -40...

An organocatalyst formed from a binaphthyl-substituted diamine and trifluoromethanesulfonic acid exhibited unprecedented levels of exo selectivity in the Diels-Alder reaction of alpha,beta-unsaturated aldehydes with cyclopentadiene. A novel axially chiral diamine was also designed as an organocatalyst for an asymmetric variant of this reaction, in which the desired cycloadducts were formed with...

This work describes the Diels-Alder reaction of the naturally occurring substituted butadiene, myrcene, with a range of different naturally occurring and synthetic dienophiles. The synthesis of the Diels-Alder adduct from myrcene and acrylic acid, containing surfactant properties, was scaled-up in a plate-type continuous-flow reactor with a volume of 105 mL to a throughput of 2.79 kg of the fin...

The Diels–Alder (DA) reaction is regarded as quite a useful strategy in organic and macromolecular syntheses.

Density Functional Theory has been used to model the Diels-Alder reactions of the fullerene fragments triindenetriphenilene and pentacyclopentacorannulene with ethylene and 1,3-butadiene. The purpose is to prove the feasibility of using Diels-Alder cycloaddition reactions to grow fullerene fragments step by step, and to dimerize fullerene fragments, as a way to obtain C₆₀. The dienophile charac...

The chemical crosslinking of modified nucleic acids via the Diels-Alder reaction is reported. For this purpose, 1,3-butadiene derived building blocks were incorporated into complementary oligodeoxynucleotides. Treatment of the obtained duplex with difunctional dienophiles results in the clean crosslinking of the two strands. Non-crosslinked adducts arising from a single Diels-Alder reaction of ...

This review illustrates how water, as an environmentally friendly solvent, can have significant additional benefits when it is used as a solvent for the Diels–Alder reaction. The mechanism by which the unique properties of water enhance the rate and selectivity are discussed. Also, possibilities for the achievement of further increases in rate and enantioselectivity of aqueous Diels–Alder react...

The electron-reorganization along the concerted and stepwise pathways associated with the non-polar Diels-Alder reaction between cyclopentadiene (Cp, 1) and ethylene (2) has been studied using the topological analysis of the electron localization function (ELF) at the B3LYP/6-31G(d) level of theory. ELF results for the concerted mechanism stresses that the electron-reorganization demanded on th...