Allenes as new unsaturated partners in transition metal-mediated cyclotrimerization and cycloisomerization reactions

ORGN 6

Max Malacria, malacria@ccr.jussieu.fr, Laboratoire de chimie organique,UMR 7611, Université Pierre et Marie Curie, 4, Place Jussieu / B. 229, 75005 Paris, France
Allenes are very useful unsaturated partners in synthesis. Few years ago we have shown that they were suitable moieties in the cobalt (I) mediated intramolecular cyclotrimerization with two alkynes. More recently we have shown that this reaction allowed a total transfer from axial to centered chirality and were able to apply this reaction to the synthesis of various functionnalyzed non-natural steroids. We have also described the cobalt (I) mediated cycloisomerization of allumene-ynes. Scope and limitation of this reaction will be discussed. Finally we have very recently discovered the platinum (II) catalyzed cycloisomerization of allene-ynes. This reaction is very substrate dependant and lead selectively either to hydrindienes adducts, vinyl allenes or trienes. The mechanism of this reaction will be discussed.

 

Allenes in Synthesis
8:00 AM-12:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C303/304/305, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006