The furan-maleimide Diels-Alder chemistry has emerged as an important tool to design thermo-reversible click networks. This not only preserves the strong and robust properties of thermo-sets rubbers, but also makes it possible cleave crosslinks at non-degradative temperatures, or in other words recycle them. In this work a new reaction is reported networks, which Double-Diels-Alder (DDA), known...

Computational studies show that the base-mediated intramolecular Diels-Alder of tryptamine-derived Zincke aldehydes, used as a key step in the synthesis of the Strychnos alkaloids norfluorocurarine and strychnine, proceeds via a stepwise pathway. The experimentally determined importance of a potassium counterion in the base is explained by its ability to preorganize the Zincke aldehyde diene in...

Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio- and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentameth...

The Diels–Alder (DA) reaction (or “diene synthesis”) between a diene and a dienophile generates two s bonds stereoselectively and up to four chiral centers in a single step to afford six-membered cyclic compounds. This cycloaddition reaction named after Professor Otto Paul Hermann Diels (1876–1954) and his student Kurt Alder (1902–1958) was discovered in 1928 during studies on the reaction of b...

A sequential Diels-Alder reaction/silicon-directed [4 + 2]-annulation was developed to assemble hydroisochromene-type ring systems from menadione 2. In the first step, a Diels-Alder of the 1-silyl-substituted butadiene 1 with 2 furnished an intermediate cyclic allylsilane. Subsequently, TMSOTf promoted a [4 + 2]-annulation through trapping of an oxonium, generated by condensation between an ald...

Key words (±)-talatisamine - Diels–Alder reaction [2+2] photo-cycloaddition Lemieux–Johnson oxidation retro-aldol–aldol Wagner–Meerwein rearrangement aza-Prins

The synthesis of silaheterocycles through the first examples of an intramolecular silene Diels-Alder reaction is described.

A new chiral Brønsted acid-catalyzed aza-Diels-Alder reaction of cyclic C-acylimines with cyclopentadiene has been developed. The reaction provides optically active aza-tetracycles in good yields with high diastereo- and enantioselectivities under mild reaction conditions.