Chiral amido-phosphine-phosphinite compounds

• Main Authors: Burkart, Wolfgang, Scalone, Michelangelo, Schmid, Rudolf
• Format: Patent
• Language: English
• Published: 19.02.2002

Enantiomerically pure (R) or (S) compounds can be produced by causing compounds to undergo enantioselective reactions. Use of enantioselective catalysts which are capable of catalyzing asymmetric hydrogenations, enantioselective hydrogen displacements and allylic substitution reactions, among others, can facilitate the attainment of high optical yields. The present invention relates to novel chiral amidophosphine-phosphinite compounds and complexes of these compounds as ligands with Group VIII metals, which complexes may be used as enantioselective catalysts. Novel chiral amidophosphine-phosphinite compounds, which are present in (R) and (S) form, of the general formula wherein Rsignifies alkyl, cycloalkyl or aralkyl, Rsignifies alkyl, cycloalkyl, aralkyl or aryl and Rand Reach independently signify alkyl, cycloalkyl, aralkyl, aryl or heteroaryl or Rand Rtogether with the respective phosphorus atom signify a 9-dibenzophospholyl, 9-phosphabicyclo[3.3.1]nonyl or 9-phosphabicyclo[4.2.1]nonyl group and * denotes a chiral center, are manufactured by reacting a compound of the general formula RC(OH)-CONHR(III) with a disubstituted chlorophosphane of the general formula RRPCl (IV) in a solvent and in the presence of a base. As ligands the amidophosphine-phosphinite compounds in accordance with the invention form complexes with Group VIII transition metals, especially with rhodium, iridium, ruthenium and palladium, and optionally with further ligands, and such complexes are likewise an object of the present invention; they can be used as catalysts for enantioselective reactions, especially for asymmetric hydrogenations, enantioselective hydrogen displacements and allylic substitution reactions.