Question
What are the two starting materials for a Robinson annulation?
Answer
A Robinson annulation combines a carbon nucleophile derived from an enolizable carbonyl compound with an α,β-unsaturated ketone (an enone).
The first partner is the Michael donor: commonly an enolate from a β-keto ester or a β-diketone. The second is the Michael acceptor, such as methyl vinyl ketone. An enamine can also serve as the donor in an appropriate variant.
Why these two partners work
- The donor attacks the enone's β-carbon in a Michael addition, creating a carbon–carbon bond.
- The resulting carbonyl arrangement permits an intramolecular aldol reaction that closes a six-membered ring.
- Dehydration gives a substituted cyclohexenone.
For example, ethyl acetoacetate can supply the donor enolate and methyl vinyl ketone can supply the acceptor. The base enables enolate formation; it is not one of the two carbon-building partners.
Without a specified target structure, the answer identifies the two reactant classes rather than a unique pair of molecules.
Evidence boundary
This standalone concept question does not specify a target product. The answer describes the usual donor–enone pairing and gives an illustrative pair, not a unique retrosynthesis or a guarantee that every enolizable carbonyl/enone combination cyclizes.
Sources
These references support the concepts and methods used in the explanation above.