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Robinson annulation - Wikipedia, the free encyclopedia

Robinson annulation

From Wikipedia, the free encyclopedia

The Robinson annulation is an organic reaction used to create a six-membered ring α,β-unsaturated ketone using a ketone (or aldehyde) and methyl vinyl ketone.[1][2][3] It is named after the British chemist who discovered it, Sir Robert Robinson while at the University of Oxford.

The Robinson annulation

In addition to methyl vinyl ketone, 1-chloro-3-propanone [4][5] and isoxazoles [6] will give the same product.

Proline has been used to resolve the enantiomeric isomers of Robinson annulations.[7] The Wieland-Miescher ketone is the Robinson annulation product of 2-methyl-1,3-cyclohexanedione and methyl vinyl ketone


Contents

[edit] Reaction mechanism

Methyl vinyl ketone (or variants thereof) are essential for the annulation as they are simultaneously a Michael acceptor and able to take part in an aldol condensation. The first step in the Robinson annulation is a Michael addition followed by an aldol reaction as the annulation step in the process. The reaction then proceeds as an aldol condensation to make the desired cyclohexenone ring.

The mechanism of the Robinson annulation

[edit] Variations

[edit] Wichterle reaction

The Wichterle reaction is a variant of the Robinson annulation that replaces methyl vinyl ketone with 1,3-dichloro-cis-2-butene.[8][9]

The Wichterle reaction


[edit] References

  1. ^  Rapson, W. S.; Robinson, R.; J. Chem. Soc. 1935, 1285.
  2. ^  Bergmann, E. D.; Gingberg, D.; Pappo, R. Org. React. 1959, 10, 179. (Review)
  3. ^  Gawley, R. E. Synthesis 1976, 777-794. (Review)
  4. ^  Heathcock, C. H.; Ellis, J. E.; McMurry, J. E.; Coppolino, A. Tetrahedron Lett. 1971, 12, 4995.
  5. ^  Heathcock, C. H.; Mahaim, C.; Schlecht, M. F.; Utawanit, T. J. Org. Chem. 1984, 49, 3264. (DOI:10.1021/jo00192a004)
  6. ^  McMurry, J. E. Organic Syntheses, Coll. Vol. 6, p.781 (1988); Vol. 53, p.70 (1973). (Article)
  7. ^  Organic Syntheses, Coll. Vol. 7, p.368 (1990); Vol. 63, p.37 (1985). (Article)
  8. ^  Wichterle, O. et al. Coll. Czech. Chem. Commun. 1948, 13, 300.
  9. ^  Kobayashi, M.; Matsumoto, T. Chem. Lett. 1973, 957.
  10. Organic Syntheses, Coll. Vol. 5, p.869 (1973); Vol. 45, p.80 (1965). (Article)
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