InCl3/CyNH2 cocatalyzed carbocyclization reaction: an entry to α-disubstituted exo-methylene cyclopentanes.
An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from α-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.
E.N.S.C.P., Chimie ParisTech, UMR 7223, Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75231 Paris Cedex 05, France.
Benjamin
B
Montaignac
Maxime R
MR
Vitale
Virginie
V
Ratovelomanana-Vidal
Véronique
V
Michelet