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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 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 ...
Strained cyclooctenes and other activated alkenes react with tetrazines in an inverse electron-demand Diels-Alder followed by a retro [4+2] cycloaddition (see figure). [41] Like the other reactions of the trans-cyclooctene, ring strain release is a driving force for this reaction.
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.
The tetrazine ligation is the reaction of a trans-cyclooctene and an s-tetrazine in an inverse-demand Diels Alder reaction followed by a retro-Diels Alder reaction to eliminate nitrogen gas. [36] The reaction is extremely rapid with a second order rate constant of 2000 M −1 –s −1 (in 9:1 methanol/water) allowing modifications of ...
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.
Among the types of reactions that can be catalyzed by Lewis acids, those with carbonyl-containing substrates have received the greatest amount of attention.The first major discovery in this area was in 1960, when Yates and Eaton reported the significant acceleration of the Diels-Alder reaction by AlCl 3 when maleic anhydride is the dienophile.
The normal electronic demand for the Diels–Alder reaction calls for an electron-rich diene to react with an electron-poor olefin (or "dienophile"), while the inverse electron-demand Diels–Alder reaction takes place between the opposite case of an electron-poor diene and a very electron-rich dienophile. The photoredox case, since it takes ...