The Wiechert and Parrish groups pioneered the use of S-proline as a catalyst in this reaction.
The Wiechert and Parrish groups pioneered the use of S-proline as a catalyst in this reaction. One reagent is replaced by 1,3-dichloro-cis-2-butene in the Wichterle modification, and this reaction's second step may be replaced with a Dieckmann condensation in a similar reaction named for Hauser. Though five stereogenic centers are generated during this reaction, only three are retained as end products as two are lost during dehydration. The original racemic Wieland-Miescher ketone is principally produced in this reaction, and an alpha-trimethlysilyl variant of one of its starting reactant can be used to prevent the side reaction of base-catalyzed polymerization of that reactant, methyl vinyl ketone. This reaction results in the formation of a bicyclic alpha-beta-unsaturated ketone. For 10 points, name this reaction consisting of a Michael addition followed by an aldol condensation.
The Wiechert and Parrish groups pioneered the use of S-proline as a catalyst in this reaction.
Robinson annulation [prompt on an incomplete answer like Robinson reaction, accept "Aldol condensation" until the words "Wichterle modification"]