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Diels–Alder reaction, simplest example. In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a pericyclic reaction with a concerted mechanism.
[44] total synthesis example of corey winter olefination; CBS-type enantioselective Diels–Alder reaction has been developed using a similar scaffold to the enantioselective CBS reduction. [31] After the development of this reaction the CBS reagent proved to be a very versatile reagent for a series of several powerful synthetic transformations.
Maleic anhydride is a classic substrate for Diels-Alder reactions. [9] It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride is converted to many pesticides and pharmaceuticals.
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 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.
Release of nitrogen from six-membered, cyclic diazenes is common and often spontaneous at room temperature. Such a reaction can be utilized in click reactions where alkanes react with a 1,2,4,5-tetrazine in a diels alder then retro diels alder reaction with the loss of nitrogen. In this another example, the epoxide shown undergoes rDA at 0 °C.
The Wagner-Jauregg reaction is a classic organic reaction in organic chemistry, named after Theodor Wagner-Jauregg [] (son of Julius Wagner-Jauregg), describing the double Diels–Alder reaction of 2 equivalents of maleic anhydride with a 1,1-diarylethylene.
Oxazolidinone auxiliaries, popularized by David A. Evans, have been applied to many stereoselective transformations, including aldol reactions, [19] alkylation reactions, [20] and Diels-Alder reactions. [21] [22] The oxazolidinones are substituted at the 4 and 5 positions. Through steric hindrance, the substituents direct the direction of ...