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        Synthesis  2004(18): 3089-3091  
DOI: 10.1055/s-2004-834908
   DOI: 10.1055/s-2004-834908
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New YorkNickel-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,ω-Ene-Diene, and Acetone: Synthesis of 1,2-Disubstituted Cycloalkanes
Weitere Informationen
            
               
                  
                        
                              Received
                              28 September 2004 
                      
Publikationsdatum:
08. November 2004 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
08. November 2004 (online)

Abstract
Under nickel catalysis, 1,3,8-nonatrienes and 1,3,9-decatrienes 3 react at room temperature with dimethylzinc and acetone at the alkene and diene termini, respectively, providing 1,2-disubstituted cycloalkanes 4 in good yield. The stereoselectivities of 4 provide useful information about the mechanistic frameworks for the present reaction and related cyclization reaction of ω-dienynes 1.
Keywords
nickel - organozinc - catalysis - cyclization - diene
- 1a 
             
            Ezoe A.Kimura M.Inoue T.Mori M.Tamaru Y. Angew. Chem. Int. Ed. 2002, 41: 2784
- 1b 
             
            Kimura M.Ezoe A.Mori M.Tamaru Y. J. Am. Chem. Soc. 2004, in press
- Protocols for this type of Ni-catalyzed addition of dienes to aldehydes:
- 2a 
             
            Kimura M.Ezoe A.Shibata K.Tamaru Y. J. Am. Chem. Soc. 1998, 120: 4033
- 2b 
             
            Kimura M.Fujimatsu H.Ezoe A.Shibata K.Shimizu M.Matsumoto S.Tamaru Y. Angew. Chem. Int. Ed. 1999, 38: 397
- 2c 
             
            Sato Y.Takimoto M.Mori M. J. Am. Chem. Soc. 2000, 122: 1624
- 2d 
             
            Shibata K.Kimura M.Shimizu M.Tamaru Y. Org. Lett. 2001, 3: 2181
- 2e 
             
            Kimura M.Ezoe A.Tanaka S.Tamaru Y. Angew. Chem. Int. Ed. 2001, 40: 3600
- 2f 
             
            Sato Y.Sawaki R.Saito N.Mori M. J. Org. Chem. 2002, 67: 656
- 2g 
             
            Kimura M.Miyachi A.Kojima K.Tanaka S.Tamaru Y. J. Am. Chem. Soc. 2004, in press
- Protocols of this type Ni-catalyzed oxidative cyclization of alkynes and alkenes:
- 3a 
             
            Chowdhury SK.Amarasinghe KKD.Heeg MJ.Montgomery J. J. Am. Chem. Soc. 2000, 122: 6775
- 3b 
             
            Mahandru GM.Skauge ARL.Chowdhury SK.Amarasinghe KKD.Heeg MJ.Montgomery J. J. Am. Chem. Soc. 2003, 125: 13481
- 3c Review:  
            Montgomery J. Angew. Chem. Int. Ed. 2004, 43: 3890
- 3d 
             
            Tamao K.Kobayashi K.Ito Y. Synlett 1992, 539
- 4 
             
            Eliel EL.Wilen SH. Stereochemistry of Organic Compounds John Wiley & Sons; New York: 1994. p.776Reference Ris Wihthout Link
- 5 To the best of our knowledge, this is the first example of transition-metal catalyzed
            cyclization of 1,3,8-nonatrienes and 1,3,9-decatrienes (3) except the transition-metal catalyzed Diels-Alder reaction:  
            O’Mahony DJR.Belanger DB.Livinghouse T. Synlett 1998, 443
- 6 
             
            Günter H. NMR Spectroscopy 2nd Ed: John Wiley & Sons; Chichester: 1995.Reference Ris Wihthout Link
- 7a 
             
            Kimura M.Matsuo S.Shibata K.Tamaru Y. Angew. Chem. Int. Ed. 1999, 38: 3386
- 7b 
             
            Kimura M.Shibata K.Koudahashi Y.Tamaru Y. Tetrahedron Lett. 2000, 41: 6789
- 7c 
             
            Shibata K.Kimura M.Kojima K.Tanaka S.Tamaru Y. J. Organomet. Chem. 2001, 624: 348
 
    