Homoenolates Explained

Homoenolates are a type of functional group that have been used in synthetic organic chemistry since the 1980s. They are related to enolates, but represent an umpolung of their reactivity. Homoenolates can be formed with a variety of different metal counterions, including lithium, iron, silver, lead, titanium, tin, tellurium, zirconium, niobium, mercury, zinc, antimony, bismuth, nickel, palladium, and copper. Homoenolates stability and reactivity varies by counterion identity and other nearby functional groups. Common pathways of decomposition include proto-demetalation and β-hydride elimination. Multiple reviews on the topic of homoenolates and their reactivity have been published.[1] [2] [3] [4] [5] [6]

References

  1. Hoppe . Dieter . The Homoaldol Reaction, or How to Overcome Problems of Regio- and Stereo-selectivity . Angewandte Chemie International Edition . Wiley . 23 . 12 . 1 December 1984 . 0570-0833 . 10.1002/anie.198409321 . 932–948.
  2. Isao. Kuwajima. Eiichi. Nakamura. 1990. Metal Homoenolates from Siloxycyclopropanes. Topics Curr Chem. 155. University of Windsor.
  3. Crimmins. M. T.. Nantermet. P. G.. Homoenolates and Other Functionalized Organometallics. A Review. 1993. Organic Preparations and Procedures International. 25. 41–81. 10.1080/00304949309457932.
  4. Menon. R. S.. Biju. A. T.. Nair. V.. 7 August 2015. Recent Advances in Employing Homoenolates Generated by N-heterocyclic Carbene (NHC) Catalysis in Carbon-Carbon Bond-Forming Reactions. Chemical Society Reviews. 44. 15. 5040–5052. 10.1039/c5cs00162e. 26014054.
  5. Nikolaev. A.. Orellana. A.. 2016. Transition-Metal-Catalyzed C–C and C–X Bond-Forming Reactions Using Cyclopropanols. Synthesis. 48. 12. 1741–1768. 10.1055/s-0035-1560442.
  6. Mills. L. R.. Rousseaux. S. A. L.. Modern Developments in the Chemistry of Homoenolates. European Journal of Organic Chemistry. 2019. 2019. 6–26. 10.1002/ejoc.201801312.

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