Robinson annulation, Wichterle reaction

Figure 14. Reaction scheme for the chiral Robinson annulation using the Wichterle reagent.

Perhaps overshadowed by the earlier work of Sir Robert Robinson where methyl vinyl ketone was shown to perform the same annulation, the potential of the Wichterle reaction remained relatively untapped. Despite... 

The Wichterle reaction is a closely related variant of the more popular Robinson annulation. The reader is encouraged to read reviews of the Robinson and related annulations that are available for a more comprehensive overview of the variations that can be employed in synthesis. ... 

Due to the vast synthetic utility of annulation reactions, there are numerous analogous sequences that can be performed to reach the same class of products as the Wichterle reaction. The most notable of which is the Robinson annulation, which uses methyl vinyl ketone in place of 1,3-dichloro-2-butene. Later research has elaborated on the Wichterle reagent by constructing an extensive library of methyl vinyl ketone surrogates 9-14 that can be employed in a manner analogous to l,3-dichloro-2-butene. Despite the development of annulation reagents like 9-14, 1,3-dichloro-2-butene retains ample synthetic utility due to both its commercial availability and its ability to be trivially prepared from ethyl acetoacetate or methyl acetoacetate. ... 

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