Science of Synthesis

Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L., Science of Synthesis, (2010) 47, 579.

In an application of the Diels–Alder strategy for the synthesis of a cyclohexene, attention should focus on two main features. The first of these concerns the number, type, position, and relative orientation of substituents in the ring, and how easy it will be to manipulate them later in the synthesis of a target compound. The choice of the 1,3-diene and the dienophile is therefore of fundamental importance. For the synthesis of an optically active cyclohexenoid it is also necessary to take into account the configuration of one or both the reagents and that of the catalyst. The second main feature is related to the methodology used to perform the reaction.[‌3‌] Due to its versatility and stereospecificity, the Diels–Alder reaction is one of the most intensively investigated transformations with respect to increasing the yield, the regio- as well as stereoselectivity, and the rate of the process, or to increasing the stability of reagents and to allow a one-pot operation for a multistep reaction. Modern practical methods used are discussed earlier in the General Introduction.

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