Diels-Alder – Stereochemistry of the diene Summary

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It is possible for the diene to be either ‘cis-cis’, ‘cis-trans’ (two possibilities if the diene is unsymmetrical) or ‘trans-trans’.
‘Click’ the images below to view 3D animations of the reactions, all of which use the same simple dienophile which has no stereochemistry:

‘cis-cis’

‘cis-trans’

‘trans-trans’

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

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