Phosphoramide compound, method for producing the same, ligand, complex, catalyst and method for producing optically active alcohol

Abstract

Disclosed is a method for highly efficiently obtaining an optically active alcohol from a carbonyl compound highly enantioselectively. Also disclosed is a ligand used in such a method. Specifically, an optically active alcohol is obtained by reacting a carbonyl compound and an organozinc compound by using a ligand (L) shown below.

1 . A ligand which is a phosphoramide compound represented by general formula (8a), (8b), (9a) or (9b): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is a monovalent hydrocarbon group which is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group and an arylalkenyl group, and which may have at least one substituent; 
         R 2  and R 3  independently are monovalent hydrocarbon groups which are selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group and an arylalkenyl group, which may have at least one substituent, and which are each bound to a phosphorus atom directly or via an atom other than carbon atom; 
         R 6  is a hydrogen atom or a monovalent hydrocarbon group which is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group and an arylalkenyl group, and which may have at least one substituent; 
         R 7  is a monovalent hydrocarbon group which is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group and an arylalkenyl group, and which may have at least one substituent; 
         X is an oxygen atom or sulfur atom; and 
         B is a methylene group or carbonyl group when the ligand is represented by the general formula (8a) or (8b), and B is a carbonyl group when the ligand is represented by the general formula (9a) or (9b). 
       
     
     
         2 . The ligand according to  claim 1 , which is represented by the general formula (8a). 
     
     
         3 . The ligand according to  claim 1 , which is represented by the general formula (8b). 
     
     
         4 . The ligand according to  claim 1 , which is represented by the general formula (9a). 
     
     
         5 . The ligand according to  claim 1 , which is represented by the general formula (9b). 
     
     
         6 . A complex comprising:
 and according to  claim 1 ; and   a central metal comprising zinc atom.   
     
     
         7 . The complex according to  claim 6 , which is represented by general formula (10):
   L m ZnR 8 (ZnR 8 R 9 ) n    (10)
   wherein   L is said ligand or a compound obtained from said ligand in which the hydrogen atom on the nitrogen atom is eliminated;   R 8  and R 9  independently are monovalent hydrocarbon groups which may have at least one substituent;   m is an integer of 1 to 10; and   n is an integer of 0 to 10.   
     
     
         8 . The complex according to  claim 6 , wherein an organozinc compound represented by ZnR 8 R 9  is coordinated to said ligand,
 wherein   R 8  and R 9  independently are monovalent hydrocarbon groups which are selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group and an arylalkenyl group, and which may have at least one substituent.   
     
     
         9 . A catalyst comprising the complex according to  claim 6 . 
     
     
         10 . The catalyst according to  claim 9 , which is capable of catalyzing a synthesis of an optically active alcohol. 
     
     
         11 . The catalyst according to  claim 10 , wherein the optically active alcohol is an optically active tertiary alcohol. 
     
     
         12 . The phosphoramide compound according to  claim 1 , wherein R 6  is a hydrogen atom, an alkyl group or an arylalkyl group, and R 7  is an aryl group, an arylalkyl group or an arylalkenyl group, and R 6  and R 7  are not substituted with an oxygen atom, a nitrogen atom or a sulfur atom. 
     
     
         13 . The ligand according to  claim 2 , wherein X is a sulfur atom. 
     
     
         14 . The ligand according to  claim 2 , wherein B is a methylene group. 
     
     
         15 . The ligand according to  claim 3 , wherein X is a sulfur atom. 
     
     
         16 . The ligand according to  claim 3 , wherein B is a methylene group. 
     
     
         17 . The ligand according to  claim 4 , wherein X is a sulfur atom. 
     
     
         18 . The ligand according to  claim 4 , wherein X is an oxygen atom. 
     
     
         19 . The ligand according to  claim 5 , wherein X is a sulfur atom. 
     
     
         20 . The ligand according to  claim 5 , wherein X is an oxygen atom.