Danishefsky's diene

This diene reacts rapidly with electrophilic alkenes, such as maleic anhydride.

The diene is known to react with amines,[5] aldehydes, alkenes and alkynes.

It was first synthesized by the reaction of trimethylsilyl chloride with 4-methoxy-3-buten-2-one and zinc chloride:[8] The diene has two features of interest: the substituents promote regiospecific addition to unsymmetrical dienophiles and the resulting adduct is amenable to further functional group manipulations after the addition reaction.

High regioselectivity is obtained with unsymmetrical alkenes with a preference for a 1,2-relation of the ether group with the electron-deficient alkene-carbon.

All this is exemplified in this aza Diels-Alder reaction:[9][10] In the cycloaddition product, the silyl ether is a synthon for a carbonyl group through the enol.

Structural formula of Danishefsky's diene
Ball-and-stick model of Danishefsky's diene
Danishefsky's diene
Danishefsky's diene
Danishefsky's diene in Aza-Diels_Alder
Danishefsky's diene in Aza-Diels_Alder