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Asymmetric Diels-Alder reaction is one step in the biosynthesis of the statin lovastatin. [60] The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6.
The retro-Diels–Alder reaction (rDA reaction) is the reverse of the Diels–Alder (DA) reaction, a [4+2] cycloelimination. It involves the formation of a diene and dienophile from a cyclohexene . It can be accomplished spontaneously with heat, or with acid or base mediation.
The Diels-Alder reaction is perhaps the most important and commonly taught cycloaddition reaction. Formally it is a [4+2] cycloaddition reaction and exists in a huge range of forms, including the inverse electron-demand Diels–Alder reaction, hexadehydro Diels–Alder reaction and the related alkyne trimerisation.
The central ring can serve as a diene in Diels–Alder reactions with various dienophiles. For example, reaction with benzyne leads to 1,2,3,4-tetraphenylnaphthalene and reaction with diphenylacetylene leads to hexaphenylbenzene. [5] In this way, it is a precursor to graphene-like molecules, [6] such as coronene.
The Boger pyridine synthesis is a cycloaddition approach to the formation of pyridines named after its inventor Dale L. Boger, who first reported it in 1981. [1] The reaction is a form of inverse-electron demand Diels-Alder reaction in which an enamine reacts with a 1,2,4-triazine to form the pyridine nucleus.
Diels-Alder reaction and inverse electron demand Diels-Alder reaction [9] [10] [4+1] cycloadditions between isonitriles (isocyanides) and tetrazines [11] nucleophilic substitution especially to small strained rings like epoxy [12] and aziridines; carbonyl-chemistry-like formation of ureas but not reactions of the aldol type due to low ...
Quinones can undergo Diels–Alder reactions. [10] The quinone acts as the dienophile and reacts with a diene at a carbon-carbon double bond. In Diels–Alder reactions quinones are used as dienophiles. Historically important syntheses include cholesterol, cortisone, morphine, and reserpine. [11]
The inverse electron demand Diels–Alder reaction, or DA INV or IEDDA [1] is an organic chemical reaction, in which two new chemical bonds and a six-membered ring are formed. It is related to the Diels–Alder reaction , but unlike the Diels–Alder (or DA) reaction, the DA INV is a cycloaddition between an electron-rich dienophile and an ...