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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.
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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.
Diagram of Photocatalytic bis-enone hetero-Diels–Alder reaction. Similarly, electron-rich styrenes participate in intra- or intermolecular Diels–Alder cyclizations via a radical cation mechanism. [30] [31] [Ru(bipy) 3] 2+ was a competent catalyst for intermolecular, but not intramolecular, Diels–Alder cyclizations. This photoredox ...
The product of this step is reacted with phenyl isocyanate to form 4-Phenyl-1-carbethoxysemicarbazide (4), which is cyclized with base to form 4-Phenylurazole (5). Oxidation with tert-Butyl hypochlorite then yields PTAD ( 6 ).
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 first reaction in the sequence is a DA INV reaction between the tetrazine and vinyl acetal, followed by a retro-Diels–Alder reaction to afford a 1,2-diazine product. After several more steps, an intramolecular DA INV reaction occurs, followed again by a retro Diels-Alder in situ, to afford an indoline product. This indoline is a converted ...