Rhodium-catalyzed functionalization of sterically hindered alkenes.
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.
Gendrineau
Thomas
T
Laboratoire Charles Friedel (UMR 7223, CNRS), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris Cedex 05, France.
Genet
Jean-Pierre
JP
Darses
Sylvain
S
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D001880:Boranes; D009942:Organometallic Compounds; D012238:Rhodium