Diels-Alder reaction – Working out which product is endo

Sn2

Click on the structures above for a method for doing this.

How to determine which product is the endo product

In the reaction between hexa-2,4-diene and acrolein two stereoisomers may be formed – endo and exo. The endo product is favoured, but how can we tell which one this is? The easiest way to work this out is by drawing the reactants coming together in 3D.

 

J. Sauer, Angew. Chemie Int. Ed. English, 1967, 6, 16–33.

 

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