Reversed Robinson Annulation

Why does this pathway occur instead of the Robinson annulation when the seemingly trivial change of increasing the concentration of NaOH is made Good question. It is not clear. It seems likely that the Robinson annulation does occur first (because quick quenching helps to increase the quantity of Robinson product), but the Elcb elimination at the end of the annulation mechanism is reversible in the presence of NaOH as base. It seems likely, then, that if NaOEt were used as base instead, only the Robinson product would be observed regardless of the quantity of catalyst. 

One problem with the Robinson annulation is the reversible nature of the initial Michael addition. One solution is to use a conjugated system that is particularly prone to Michael addition and forms the product, essentially irreversibly. a-Silyl vinyl ketones have been shown to be powerful Michael acceptors.The lithium enolate of cyclohexanone reacted with conjugated ketone 559 to produce the Michael product. 560.304b jn this case, the initially formed Michael adduct was stabilized by the presence of the silyl group at the a-position, driving the reaction toward the product. Hydrolysis produced 561, which was converted to the Robinson product (562) in 80% overall yield by treatment with NaOMe/MeOH under the requisite thermodynamic conditions.304b Pq,. this sequential process is justified when compared with normal treatment... 

Propose retrosynthetic Michael [(a)] or Robinson steps [(b), (c)] to the following compounds. [Hint For (b) and (c), identify and unravel the cyclohexenone ring in a reverse annulation sequence.]... 

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