Rhodium-catalyzed functionalization of sterically hindered alkenes.

Org Lett

Laboratoire Charles Friedel (UMR 7223, CNRS), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris Cedex 05, France.

Published: January 2010

For the first time the rhodium-catalyzed 1,4-addition of organoboranes to hindered Baylis-Hillman adducts, trisubstituted alkenes, affording highly functionalized alkenes, via addition of the organoboranes and hydroxyelimination, is reported. Moreover, preliminary results have shown that, thanks to the use of a monosubstituted chiral diene ligand, enantio-enriched products were easily accessible, while chiral phosphane ligands were completely inappropriate in this reaction.

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http://dx.doi.org/10.1021/ol902646jDOI Listing

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