Chiral monophosphorus compounds

Abstract

The present invention relates to catalysts comprising chiral monophosphorus compounds and their use, the chiral monophosphorus compounds themselves and also their precursors.

1 . Compounds of the general formula (XI)  
     
       
         
         
             
             
         
       
     
     where R 1  is an unsubstituted or substituted 1,1′-biphenyl-2,2′-diyl radical and 
 Akt is chlorine, bromine, iodine or dialkylamino.  
 
   
   
       2 . A method of preparing chiral phosphonites, chiral phosphoramidites or chiral phosphites comprising providing the compounds according to  claim 1 .  
   
   
       3 . A method of conducting asymmetric 1,4-additions, asymmetric hydroformylations, asymmetric hydrocyanations, asymmetric Heck reactions and asymmetric hydrogenations comprising providing the compounds of  claim 1 .  
   
   
       4 . Catalysts comprising transition metal complexes of chiral monophosphorus compounds of the general formula (I),  
     
       
         
         
             
             
         
       
     
     where 
 R 1  is an unsubstituted or substituted 1,1′-biphenyl-2,2′-diyl radical and  
 R 2  is a radical selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy and tertiary amino.  
 
   
   
       5 . Catalysts according to  claim 4 , which are produced from chiral monophosphorus compounds of the general formula (I) and metal compounds.  
   
   
       6 . Process for preparing chiral compounds, comprising catalyzing the preparation with catalysts according to  claim 4 .  
   
   
       7 . Process for preparing chiral compounds, comprising catalyzing the preparation with catalysts according to  claim 5 .  
   
   
       8 . Process for the asymmetric hydrogenation of substrates, comprising catalyzing the hydrogenation with catalysts according to  claim 4 .  
   
   
       9 . Process for the asymmetric hydrogenation of substrates, comprising catalyzing the hydrogenation with catalysts according to  claim 5 .  
   
   
       10 . Process according to  claim 8 , wherein catalysts used are catalysts produced from chiral monophosphorus compounds according to any of claims  1  and metal compounds of the general formula (XIIIe)  
       [M(B 3 ) 2 ]An   (XIIIe),  
     where 
 M is rhodium and  
 B 3  is a (C 4 -C 12 )-diene such as norbornadiene or 1,5-cyclooctadiene and  
 An is a noncoordinating or weakly coordinating anion.  
 
   
   
       11 . Process according to  claim 8 , which is carried out in at least one solvent selected from the group consisting of chlorinated alkanes, C 1 -C 6 -alcohols aromatic hydrocarbons, ketones and carboxylic esters.  
   
   
       12 . Process as claimed in  claim 8 , which is carried out at temperatures of from −20 to 200° C.  
   
   
       13 . Process according to  claim 8 , which is carried out under a hydrogen pressure of from 0.1 to 200 bar.  
   
   
       14 . Process according to  claim 8 , wherein the amount of the metal compound used or of the transition metal complex used is from 0.001 to 5 mol % based on the substrate used.  
   
   
       15 . Process according to  claim 6 , wherein the substrate conversion rate is above 1 000 h −1 .  
   
   
       16 . A method of preparing chiral active compounds in pharmaceuticals and agrochemicals or intermediates thereof comprising providing the compounds of prepared according to the process of  claim 15.