Rubottom Oxidation

Rubottom Oxidation

06 October, 2015 / by / in Reactions
4531
Overall Score4
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • Criteria #4
  • Criteria #5

  • General Characteristics

The epoxidation of silyl enol ethers with oxidants such as mCPBA and dioxirane leads to rearrangement into α-silyloxyketones. This reaction is used commonly to introduce a hydroxyl group to the α-position of ketones.

  • General References

・ Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319. doi:10.1016/S0040-4039(01)92153-7
・ Brook, A. G.; Macrae, D. M. J. Organomet. Chem. 1974, 77, C19. doi:10.1016/S0022-328X(00)81332-7
・ Hassner, A.; Reuss, R. H.; Pinnick, H. W. J. Org. Chem. 1975, 40, 3427. DOI: 10.1021/jo00911a027

  • Reaction Mechanism

rubottom_2.gif

  • Examples

The regioselective α-hydroxylation of a complex ketone in the synthesis of (-)-stenine.[1]

rubottom_3.gif

  • Experimental Procedure

  • Experimental Tips

  • References

[1] Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem. Int. Ed. 1996, 35, 904. DOI: 10.1002/anie.199609041

  • Related Reactions

 

  • Related Books

  • External Links

,