To use all functions of this page, please activate cookies in your browser.
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
Danishefsky’s diene (Kitahara diene) is an organic compound and a diene with the formal name trans-1-methoxy-3-trimethylsilyloxy-l,3-butadiene. Because the diene is very electron-rich it is used as a very reactive reagent in Diels-Alder reactions. The OMe group allows for the Diels-Alder reaction to be made regiospecific, since the electrophilic carbon to which it is attached will react preferentially with the most nucleophilic atom of a dienophile.
Additional recommended knowledge
Its reaction with maleic anhydride is a fast one.
In a reaction with an alkene the silyl ether is a synthon for a carbonyl group through an enol while the ether group is susceptible to an elimination reaction and capable of forming a new alkene group. In addition high regioselectivity is obtained with unsymmetrical alkenes with a preference for an 1,2-relation of the ether group with the electron-deficient alkene-carbon. All this is exemplified in this Aza Diels-Alder reaction  :
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Danishefsky’s_diene". A list of authors is available in Wikipedia.|