Conia-Ene Reaction

Conia-Ene Reaction

Overall Score4
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • Criteria #4
  • Criteria #5
  • General Characteristics

In the Conia-ene reaction, the enol and the alkene or alkyne parts of an unsaturated carbonyl compound react and undergo intramolecular cyclization.

  • General References

  • Reaction Mechanism

  • Examples

In 2004, Toste reported the gold-catalyzed Conia-ene type reaction of β-ketoesters containing unactivated alkyne.[1] The enantioselective version of this reaction using Pd(II)/Yb(III) dual catalyst system was reported a year later.[2] 

  • Experimental Procedure

  • Experimental Tips

  • References

[1] Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc2004126, 4526. DOI: 10.1021/ja049487s[2] Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc., 2005127, 17168. DOI: 10.1021/ja055059q

  • Gao, Q.; Zheng, B. -F.; Li, J.-H.; Yang, D. Org. Lett20057, 2185. DOI: 10.1021/ol050532q
  • Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005127, 17168. DOI: 10.1021/ja055059q
  • Urabe, F.; Nagashima, S.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. J Org Chem 201378, 3847. DOI: 10.1021/jo400263w
  • Related Reactions

  • Related Books

[amazonjs asin=”3642692354″ locale=”US” title=”Intramolecular Diels-Alder and Alder Ene Reactions (Reactivity and Structure: Concepts in Organic Chemistry)”]

  • External Links