Diels-Alder: E,Z (trans, cis) Diene – Stereochemistry Of The Diene

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There are very few examples of this kind of reaction due to the fact that it is difficult to make E,Z dienes. The diene reacts with an interesting dienophile: DEAD (diethyl azodicarboxylate). As expected, the resulting six-membered ring has trans stereochemistry with the methoxy group on the opposite face of the six-membered ring to the alkyl chain.

Examples of sterochemistry in trans,trans (E,E) and cis,cis (Z,Z) dienes.

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

 

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