Diels-Alder Synthesis

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Kurt Alder’s contribution to the fields of chemistry is associated with diene synthesis. Evidence of his first report was in Otto Diels’s laboratory in 1928. Diels synthesis is a synthetic method, which is referred as the Diels-Alder reaction. The method involves the addition of diene to dienophiles. An example would be the double bonds on adjacent carbon atoms. Another example of diene synthesis is the addition of butadiene to maleic anhydride. Dienes are compounds with conjugated unsaturation. Dienes of the Diels-Alder reaction may either be cyclic or open-chain. It also hosts many substituents( an atom taking the place of another atom to occupy a specified position in a molecule), with the requirement of being able to exist in s-cis conformation. Dienophiles are compounds with an ethyenic double or acetylenic triple bond, activated …show more content…
One of the common examples of use of the Diels-Alder Reaction in total synthesis was in the syntheses of cortisone and cholesterol in 1952, at a Woodward landmark. Diene synthesis has also been applied to systems such as carbonyls and imines to provide to corresponding hetero cycles. This is referred to as the hetero-Diels-Alder reaction. An inverse reaction of this process also can be made and it is referred to as the retro-Diels-Alder reaction. The retro-Diels-Alder reaction is the forming of a diene and dienophiles from a cyclohexene, which is a liquid unsaturated cyclic hydrocarbon made by dehydrating cyclohexanol. The reaction can be accomplished with heat, acid, or with base mediation. From 1929, this process was applied to the detection of cyclohexadienes. This released ethylene and aromatic compounds as a result of the reaction between cyclohexadienes and acetylenes through a sequence of the Diels-Alder or retro-Diels
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