Polyethylene terephthalate (PET) is a polymeric material with high global demand. Conventionally, PET is produced from fossil-fuel-based materials. Herein, we explored the feasibility of a sustainable method for PET production by using solely bio-renewable resources. Specifically, 2,5-dimethylfuran (derived from lignocellulosic biomass through 5-(hydroxymethyl)furfural) and acrolein (produced f...

The nitro oxanorbornene adduct derived from the Diels-Alder reaction of ethyl (E)-3-nitroacrylate and furan provides a versatile template for the stereoselective synthesis of hydroxylated derivatives of 2-aminocyclohexanecarboxylic acid (ACHC).

A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.

The first examples of hetero Diels-Alder reaction of masked o-benzoquinones with nitroso dienophiles leading to novel and highly functionalized heterocycles, which are potential intermediates for nitrogenous natural products are reported.

Both enantiomers of FF8181-A were synthesized through optical resolution from the known Diels-Alder reaction product in 15 steps. The absolute configuration of the natural product was determined to be 1S,5S,5aS,9aS,9bS.

Inverse electron demand Diels-Alder reaction of functionalized 5,5'-bi-1,2,4- triazines with bicyclo[2.2.1]hepta-2,5-diene in boiling p-cymene leads to a range of 6,6'- disubstituted-2,2'-bipyridines in good yield.

A highly reactive and acidic chiral Brønsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels-Alder reaction of alpha,beta-unsaturated ketone with silyloxydiene was demonstrated using this chiral Brønsted acid catalyst.

The GPR30 agonist probe G-1 and structural analogs were efficiently synthesized using multicomponent or stepwise Sc(III)-catalyzed aza-Diels-Alder cyclization. Optimization of solvent and reaction temperature provided enhanced endo-diastereoselectivity.

BACKGROUND In the present study, we show the correlation of quantum chemical structural descriptors with the activation barriers of the Diels-Alder ligations. A set of 72 non-catalysed Diels-Alder reactions were subjected to quantitative structure-activation barrier relationship (QSABR) under the framework of theoretical quantum chemical descriptors calculated solely from the structures of dien...