Robinson Annulation

W. S. Rapson, R. Robinson, J. Chem. Soc. 1935, 1285.

Formation of six-membered ring α,β-unsaturated ketones by the addition of cyclohexanones to methyl vinyl ketone (or simple derivatives of methyl vinyl ketone) or its equivalents, followed by an intramolecular aldol condensation, q.v.:



Early review: R. E. Gawley, Synthesis 1976, 777-794. Improved methodology: T. Sato et al., Tetrahedron Letters 31, 1581 (1990). Stereochemical study: C. Nussbaumer, Helv. Chim. Acta 73, 1621 (1990). Synthetic applications: R. V. Bonnert et al., J. Chem. Soc. Perkin Trans. I 1991, 1225; S. Kim, P. L. Fuchs, J. Am. Chem. Soc. 115, 5934 (1993). Cf. Michael Reaction; Wichterle Reaction.