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        Synlett  2002(7): 1128-1130
DOI: 10.1055/s-2002-32598
   DOI: 10.1055/s-2002-32598
LETTER
© Georg Thieme Verlag Stuttgart · New YorkA Simple Protocol for the One Pot Synthesis of Chiral Secondary Benzylic Alcohols by Catalytic Enantioselective Reduction of Aromatic Ketones
Further Information
            
               
                  
                        
                              Received
                              13 February 2002 
                      
Publication Date:
07 February 2007 (online)
            
         
      
   Publication History
Publication Date:
07 February 2007 (online)
Abstract
A simple and efficient protocol for the one-pot catalytic enantioselective reduction of prochiral aromatic ketones mediated by in situ prepared catalysts derived from (S)-(-)-diphenyl-pyrrolidin-2-yl-methanol, is reported.
Key words
enantioselective reduction - chiral alcohols - oxazaborolidines - chiral catalysts - one-pot reaction
- 1 
             
            
Hirao A.Itsuno S.Nakahama S.Yamazaki N. J. Chem. Soc., Chem. Commun. 1981, 315 - 2 
             
            
Corey EJ.Bakshi RK.Shibata S. J. Am. Chem. Soc. 1987, 109: 5551 - 3a 
             
            
Singh VK. Synthesis 1992, 605 - 3b 
             
            
Martens J.Wallbaum S. Tetrahedron: Asymmetry 1992, 3: 1475 - 3c 
             
            
Deloux L.Srebnik M. Chem. Rev. 1993, 93: 763 - 3d 
             
            
Corey EJ.Helal CJ. Angew. Chem. Int. Ed. 1998, 37: 1987 - 4a 
             
            
Gamble MP.Studley JR.Wills M. Tetrahedron Lett. 1996, 37: 2853 - 4b 
             
            
Gamble MP.Smith AR.Wills M. J. Org. Chem. 1998, 63: 6063 - 4c 
             
            
Buono G.Chiodi O.Wills M. Synlett 1999, 377 - 5 
             
            
Yang G.-S.Hu J.-B.Zhao G.Ding Y.Tang M.-H. Tetrahedron: Asymmetry 1999, 10: 4307 - 6a 
             
            
Manju K.Trehan S. Tetrahedron: Asymmetry 1998, 9: 3365 - 6b 
             
            
Fujisawa T.Onogawa Y.Shimizu M. Tetrahedron Lett. 1998, 39: 6019 - 7a 
             
            
Mathre DJ.Jones TK.Xavier LC.Blacklock TJ.Reamer RA.Mohan JJ.Turner JET.Hoogsteen K.Baum MW.Grabowski EJ. J. Org. Chem. 1991, 56: 751 - 7b 
             
            
Jones TK.Mohan JJ.Xavier LC.Blacklock TJ.Mathre DJ.Sohar P.Jones ETT.Reamer RA.Roberts FE.Grabowski EJ. J. Org. Chem. 1991, 56: 763 - 7c 
             
            
Fujisawa T.Onogawa Y.Shimizu M. Tetrahedron Lett. 1998, 39: 6019 - 7d 
             
            
Nevalainen V. Tetrahedron: Asymmetry 1991, 2: 827 ; and references cited therein - 8a 
             
            
Cho BT.Ryu MH. Bull. Korean Chem. Soc. 1994, 15: 1027 - 8b 
             
            
Hong Y.Nie X.Zepp CM. Tetrahedron Lett. 1994, 35: 6631 - 8c 
             
            
Caze C. React. Funct. Polymers 1995, 26: 85 - 9a 
             
            
Shi Y.-J.Cai D.Dolling U.-H.Douglas AW.Tschaen DM.Verhoeven TR. Tetrahedron Lett. 1994, 35: 6409 - 9b 
             
            
Tschaen DM.Abramson L.Cai D.Desmond R.Dolling U.-H.Frey L.Karady S.Shi Y.-J.Verhoeven TR. J. Org. Chem. 1995, 60: 4324 - 10 
             
            
Salunkhe AM.Burkhardt ER. Tetrahedron Lett. 1997, 38: 1523 - 11 
             
            
Masui M.Shioiri T. Synlett 1997, 273 - 12a 
             
            
Pinho P.Guijarro D.Andersson PG. Tetrahedron 1998, 54: 7897 - 12b 
             
            
Brandt P.Andersson PG. Synlett 2000, 1092 - 13 
             
            
Brown CA.Krishnamurthy S. J. Org. Chem. 1978, 43: 273 - 14 
             
            
Kaufman TS.Ponzo VL.Zinczuk J. Org. Prep. Proc. Int. 1996, 28: 487 - 15 
             
            
Ponzo VL.Kaufman TS. Tetrahedron Lett. 1995, 36: 9105