Conia-Ene Reaction

• 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

•  Rouessac, F. Tetrahedron Lett. 1965, 6, 3319. doi:10.1016/S0040-4039(01)89202-9
•  Conia, J. M., Le Perchec, P. Synthesis 1975, 1. doi:10.1055/s-1975-23652
•  Kende, A. S.; Newbold, R. C. Tetrahedron Lett. 1989, 30, 4329. doi:10.1016/S0040-4039(00)99352-3

• 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. Soc. 2004, 126, 4526. DOI: 10.1021/ja049487s[2] Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc., 2005, 127, 17168. DOI: 10.1021/ja055059q

• Gao, Q.; Zheng, B. -F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185. DOI: 10.1021/ol050532q
• Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 17168. DOI: 10.1021/ja055059q
• Urabe, F.; Nagashima, S.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. J Org Chem 2013, 78, 3847. DOI: 10.1021/jo400263w

• Related Reactions

• Carbonyl-Ene Reaction (Prins Reaction)
• Alder Ene Reaction

• Related Books

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

• External Links

• Conia-Ene Reaction （organic-chemistry.org）
• Ene Reaction- Wikipedia
• Catalytic Enantioselective Conia-Ene Reaction （organic-chemistry.org）

conia ene reaction, cyclization