Sulphonylated Diphenylethylenediamines, Method for Their Preparation and Use in Transfer Hydrogenation Catalysis

Abstract

A diamine of formula (I) is described in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X 1 , X 2 , Y 1 , Y 2 or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group. The chiral diamine may be used to prepare catalysts suitable for use in transfer hydrogenation reactions.

1 . A diamine of formula (I) 
     
       
         
         
             
             
         
       
       in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X 1 , X 2 , Y 1 , Y 2  or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group. 
     
   
   
       2 . The diamine according to  claim 1  wherein A is hydrogen. 
   
   
       3 . The diamine according to  claim 1  wherein B is a substituted or unsubstituted aryl group. 
   
   
       4 . The diamine according to  claim 1  wherein X 1 , X 2 , Y 1  and Y 2  are hydrogen and Z is a C1-C10 alkyl, alkaryl, cycloalkyl, aralkyl or alkoxy substituting group. 
   
   
       5 . The diamine according to  claim 4  wherein Z is methyl. 
   
   
       6 . The diamine according to  claim 4  wherein Z is methoxy. 
   
   
       7 . The diamine according to  claim 1  wherein the diamine is homochiral. 
   
   
       8 . The method for preparing a diamine of formula (I) as claimed in  claim 1  comprising the steps of
 a) forming a substituted spiroimidazole from a substituted diketone of formula (II),   b) reducing the substituted spiroimidazole to form a substituted diamine,   c) optionally resolving the substituted diamine to an enantiomerically enriched form, and   d) sulphonylating the substituted diamine.   
     
       
         
         
             
             
         
       
     
   
   
       9 . A catalyst comprising the reaction product of a diamine of formula (I) as claimed in  claim 1  and a compound of a metal selected from the list consisting of Ru, Rh, Ir, Co, Ni, Fe, Pd or Pt. 
   
   
       10 . The catalyst according to  claim 9  wherein the metal compound is [MX 2 (arene)] 2  where M=Rh or Ru and X=halogen. 
   
   
       11 . A method comprising contacting the catalyst according to  claim 9  with a compound and performing a transfer hydrogenation reaction. 
   
   
       12 . The method according to  claim 11  wherein the compound is a cyclic ketone. 
   
   
       13 . The diamine according to  claim 2  wherein B is a substituted or unsubstituted aryl group. 
   
   
       14 . The diamine according to  claim 2  wherein X 1 , X 2 , Y 1 , and Y 2  are hydrogen and Z is a C1-C10 alkyl, alkaryl, cycloalkyl, aralkyl or alkoxy substituting group. 
   
   
       15 . The diamine according to  claim 3  wherein X 1 , X 2 , Y 1  and Y 2  are hydrogen and Z is a C1-C10 alkyl, alkaryl, cycloalkyl, aralkyl or alkoxy substituting group. 
   
   
       16 . The diamine according to  claim 13  wherein X 1 , X 2 , Y 1  and Y 2  are hydrogen and Z is a C1-C10 alkyl, alkaryl, cycloalkyl, aralkyl or alkoxy substituting group. 
   
   
       17 . The diamine according to  claim 14  wherein Z is methyl or methoxy. 
   
   
       18 . The diamine according to  claim 15  wherein Z is methyl or methoxy. 
   
   
       19 . The diamine according to  claim 16  wherein Z is methyl or methoxy. 
   
   
       20 . The diamine according to  claim 19  wherein the diamine is homochiral.