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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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Organic Chemistry/Print version; Structural Biochemistry/Organic Chemistry; Structural Biochemistry/Volume 1; Usage on en.wiktionary.org Diels-Alder reaction; Usage on es.wikipedia.org Reacción de Diels-Alder; Reacciones de alquenos; Usage on eu.wikipedia.org Diels-Alder erreakzio; Usage on fi.wikipedia.org Sykloadditio; Diels–Alder-reaktio
The synchronous 6π-electron Diels-Alder reaction is a [π 4 s + π 2 s]-cycloaddition (i.e. suprafacial with respect to both components), as exemplified by the reaction to the right. The Diels-Alder reaction is suprafacial with respect to both components. Thus as the total number of antarafacial components is 0, which is even, the reaction is ...
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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 ...
For example, an analog for the Diels-Alder reaction is the quadricyclane-DMAD reaction: In the (i+j+...) cycloaddition notation i and j refer to the number of atoms involved in the cycloaddition. In this notation, a Diels-Alder reaction is a (4+2)cycloaddition and a 1,3-dipolar addition such as the first step in ozonolysis is a (3+2)cycloaddition.
Depending on the substrate chosen, the HDDA reaction can be initiated thermally or by the addition of a suitable catalyst, often a transition metal. [1] [2] [4] [5] The prevailing mechanism for the thermally-initiated HDDA reaction is a [4+2] cycloaddition between a conjugated diyne (1,3-dialkyne) and an alkyne (often referred to as a diynophile in analogy to the Diels–Alder dienophile) to ...