Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes

Qiang Gao; Bao-Fu Zheng; Jin-Heng Li; Dan Yang

doi:10.1021/ol050532q

Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes

Org Lett. 2005 May 26;7(11):2185-8. doi: 10.1021/ol050532q.

Authors

Qiang Gao¹, Bao-Fu Zheng, Jin-Heng Li, Dan Yang

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, PR China.

PMID: 15901165
DOI: 10.1021/ol050532q

Abstract

[reaction: see text]. We have discovered a Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes. In the presence of Ni(acac)2 and Yb(OTf)3, various acetylenic 1,3-dicarbonyl compounds underwent Conia-ene reaction to give mono- and bicyclic olefinic cyclopentanes. A mechanism involving the enol-yne-Ni complex formation is proposed and supported by deuterium-labeling experiments.