ABSTRACT
This Account outlines the preparation and application of a class of phosphine ligands based upon the trans-2,5-disubstituted phospholane moiety. The modular nature of these ligands has allowed facile variation of both phospholane substituent and backbone structure, thus providing access to a series of ligands. Bidentate bis(phospholane) ligands have been found to be very useful in asymmetric catalytic hydrogenation reactions. In particular, we highlight the versatility of highly efficient bis(phospholane)rhodium catalysts that allow enantioselective hydrogenation to produce a diverse range of compounds containing C-N, C-O, and C-C stereogenic centers.
Subject(s)
Phosphines/chemistry , Amides/chemistry , Catalysis , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/chemistry , Hydrogenation , Ligands , Molecular Conformation , Organometallic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Phosphines/chemical synthesis , Rhodium/chemistry , StereoisomerismABSTRACT
Enantioselective catalysts produce organic compounds in enantiomerically enriched form. They are highly efficient tools for the synthesis of biologically active materials, such as pharmaceuticals and crop-protection chemicals, in which enantiomeric purity can be critical. The design of chiral ligands is the key to developing new enantioselective catalysts. Three unusual families of ligands have been used to develop practical technology for enantioselective hydrocyanation of olefins, ring-opening of epoxides, and hydrogenation of various compounds.
