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2.5.5.2.2 Carbonyl-Ene Reactions

DOI: 10.1055/sos-SD-213-00165

Kaposi, M.; Witt, J.; Cokoja, M.; Kühn, F. E.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20142296.

The ene reaction is the “indirect substituting addition”[‌27‌] of a compound with a double bond (enophile) to an alkene possessing an allylic hydrogen (ene). If the enophile is a carbonyl compound, such as formaldehyde, the reaction is referred to as a “carbonyl-ene” reaction. The reaction involves allylic shift of one double bond, transfer of the allylic hydrogen to the carbonyl, and bonding between the two unsaturated termini.[‌28‌] It is mechanistically related to the Diels–Alder addition, but the activation energy for an ene reaction is higher due to the necessary cleavage of a C—H σ-bond.[‌29‌] Therefore it is induced either thermally or catalytically using a Lewis acid.

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