Ene reaction
Reaction in organic chemistry / From Wikipedia, the free encyclopedia
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In organic chemistry, the ene reaction (also known as the Alder-ene reaction by its discoverer Kurt Alder in 1943) is a chemical reaction between an alkene with an allylic hydrogen (the ene) and a compound containing a multiple bond (the enophile), in order to form a new σ-bond with migration of the ene double bond and 1,5 hydrogen shift. The product is a substituted alkene with the double bond shifted to the allylic position.[1]
This transformation is a group transfer pericyclic reaction,[2] and therefore, usually requires highly activated substrates and/or high temperatures.[3] Nonetheless, the reaction is compatible with a wide variety of functional groups that can be appended to the ene and enophile moieties. Many useful Lewis acid-catalyzed ene reactions have been also developed, which can afford high yields and selectivities at significantly lower temperatures, making the ene reaction a useful C–C forming tool for the synthesis of complex molecules and natural products.