Ferrier carbocyclization

Not to be confused with the Ferrier rearrangement, a reaction discovered by the same chemist.

The Ferrier carbocyclization (or Ferrier II reaction) is an organic reaction that was first reported by the carbohydrate chemist Robert J. Ferrier in 1979.[1][2] It is a metal-mediated rearrangement of enol ether pyrans to cyclohexanones. Typically, this reaction is catalyzed by mercury salts, specifically mercury(II) chloride.

Several reviews have been published.[3][4]

  1. ^ Ferrier, RJ (1979). "Unsaturated carbohydrates. Part 21. A carbocyclic ring closure of a hex-5-enopyranoside derivative". J. Chem. Soc., Perkin Trans. 1: 1455–1458. doi:10.1039/p19790001455.
  2. ^ Blattner, RJ; Ferrier, RJ (1986). "Direct synthesis of 6-oxabicyclo[3.2.1]octane derivatives from deoxyinososes". Carbohydr. Res. 150: 151–162. doi:10.1016/0008-6215(86)80012-X.
  3. ^ Ferrier, RJ; Middleton, S (1993). "The conversion of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes". Chem. Rev. 93 (8): 2779–2831. doi:10.1021/cr00024a008.
  4. ^ Marco-Contelles, J; Molina, Maria T.; Anjum, S (2004). "Naturally Occurring Cyclohexane Epoxides: Sources, Biological Activities, and Synthesis†". Chem. Rev. 104 (6): 2857–2900. doi:10.1021/cr980013j. PMID 15186183.