83 Robinson Annulation

Fig. 83.1: The Robinson annulation mechanism.265

265 The Robinson annulation mechanism is a cascade of the Michael conjugate addition (see Chap-
ter 59), followed by the aldol condensation, and finally E1cB elimination (see Chapter 6).

https://doi.org/10.1515/9783110608373-083
 83 Robinson Annulation   187

Fig. 83.2: The aldol condensation mechanism.266

Fig. 83.3: The discovery of the Robinson annulation.267

266 The base-catalyzed aldol condensation can yield β‒hydroxy aldehydes (aldols) or ketones. The
formed aldols can undergo an elimination and yield crotonaldehydes (the croton condensation =
crotonation) [1].
267 The reaction was likely first described around 1935 [83a]. In 1947, Sir Robert Robinson received
the Nobel Prize in Chemistry for his work related to alkaloids [83b].