Elimination versus ring opening: A convergent route to alkylidene- cyclobutanes

Julien Brioche (1) , Michal Michalak (1) , Béatrice Quiclet-Sire (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition-elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring. © 2011 American Chemical Society.

Domaines: Chimie organique

Julien Brioche, Michal Michalak, Béatrice Quiclet-Sire, Samir Z. Zard. Elimination versus ring opening: A convergent route to alkylidene- cyclobutanes. Organic Letters, 2011, 13 (23), pp.6296-6299. ⟨10.1021/ol202798r⟩. ⟨hal-00950020⟩