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Robinson Annulation
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The Robinson Annulation is a C–C bond-forming reaction for the synthesis of six-membered rings. It combines a Michael addition followed by an Aldol condensation. It is used in organic chemistry for ring formation to create 6 membered rings. For example, the reaction of a ketone such as cyclohexanone with an α,β-unsaturated ketone such as methyl vinyl ketone to give the corresponding bicyclic enone. • General features: • 1. It can be both acid- and base-catalyzed. • 2. It is a one-pot reaction; however, higher yields are usually obtained when the Michael adduct is isolated and then subjected to the aldol reaction. • Reaction mechanism: • The mechanism involves the Michael addition of the enolate across the double bond of the α,β-unsaturated ketone to produce the Michael adduct (a 1,5-diketone). Then, the intramolecular Aldol reaction yields a cyclic β-hydroxy ketone that is immediately dehydrated. • Pinterest: • https://www.pinterest.es/pin/67166973... • References: • https://nrochemistry.com/robinson-ann... • Seminal publication: • J. Chem. Soc., 1935, 1285-1288. https://doi.org/10.1039/JR9350001285 • Similar reactions: • Aldol reaction. Aldol condensation: • Aldol Addition and Condensation • Michael Addition reaction: • Michael Addition • Claisen Condensation: • Claisen Condensation • Hajos-Parrish reaction (the enantioselective version of the Robinson Annulation)
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