Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.
The development of an efficient catalytic system for enantioselective carbon-carbon bond formation by 1,4-addition of organometallic reagents (organolithium, Grignard, and organozinc reagents) to enones is a major challenge in organic synthesis. This Account presents the breakthrough realized in this field using chiral phosphoramidite ligands for copper-catalyzed dialkylzinc additions. Applications in catalytic routes to cycloalkanones as well as tandem and annulation procedures with excellent enantioselectivities are discussed.
Feringa
B L
BL
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008024:Ligands; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis; D015032:Zinc / Q000737:chemistry
D006844:Hydrocarbons, Cyclic; D007659:Ketones; D008024:Ligands; D009943:Organophosphorus Compounds; D013256:Steroids; D003300:Copper; D015032:Zinc