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        Synlett  2008(7): 1081-1085  
DOI: 10.1055/s-2008-1072655
   DOI: 10.1055/s-2008-1072655
LETTER
© Georg Thieme Verlag Stuttgart · New YorkNew Cationic Bisoxazoline-Au(III) Complex Catalyzed Cycloisomerization of 1-Allenyl-1-ethynyl Acetate
Further Information
            
               
                  
                        
                              Received
                              17 January 2008 
                      
Publication Date:
28 March 2008 (online)
            
         
      
   Publication History
Publication Date:
28 March 2008 (online)

Abstract
Treatment of 1-allenyl-1-diethynyl acetates in the presence of a Au or Pt catalyst (5 mol%) in toluene at room temperature, followed by methanolysis, gave 4-methylene-2-cyclopentenones. The new cationic bisoxazoline (box)-Au(III) complex {(S,S)-Phbox- or [(R,R)-Bnbox AuCl2]SbF6} accelerated the reaction, providing the products in moderate yield (60-69%).
Key words
1-allenyl-1-diethynyl acetates - 4-alkylidene-2-cyclopentenones - cationic box-Au(III) complex
- 1a 
             
            Handbook of Organopalladium Chemistry for Organic Synthesis
              
            Vol. 2: 
             
            Negishi E. Wiley; New York: 2002. p.2309
- For recent reviews, see:
- 1b 
             
            Nakamura I.Yamamoto Y. Chem. Rev. 2004, 104: 2127
- 1c 
             
            Zeni G.Larock RC. Chem. Rev. 2004, 104: 2285
- 1d 
             
            Soderberg BCG. Coord. Chem. Rev. 2004, 248: 1085
- 1e 
             
            Vizer SA.Yerzhanov KB.Quntar AAAA.Dembitsky VM. Tetrahedron 2004, 60: 5499
- 1f 
             
            Muzart J. Tetrahedron 2005, 61: 5955
- 1g 
             
            Asao N. Synlett 2006, 1645
- 2a 
             
            Marion N.Diez-Gonzalez S.Fremont P.Noble AR.Nolan SP. Angew. Chem. Int. Ed. 2006, 45: 3647
- 2b 
             
            Wang S.Zhang L. J. Am. Chem. Soc. 2006, 128: 8414
- 2c 
             
            Pujanauski BG.Prasad BAB.Sarpong R. J. Am. Chem. Soc. 2006, 128: 6786
- 2d 
             
            Zhang L.Wang S. J. Am. Chem. Soc. 2006, 128: 1442
- 2e 
             
            Zhao J.Hughes CO.Toste FD. J. Am. Chem. Soc. 2006, 128: 7436
- 2f 
             
            Zhang L. J. Am. Chem. Soc. 2005, 127: 16804
- 2g 
             
            Johansson MJ.Gorin DJ.Staben ST.Toste FD. J. Am. Chem. Soc. 2005, 127: 18002
- 2h 
             
            Cariou K.Mainetti E.Fensterbank L.Malacria M. Tetrahedron 2004, 60: 9745
- 3a 
             
            Rautenstrauch V. J. Org. Chem. 1984, 49: 950
- 3b 
             
            Shi X.Gorin DJ.Toste FD. J. Am. Chem. Soc. 2005, 127: 5802
- 4a 
             
            Kato K.Teraguchi R.Kusakabe T.Motodate S.Yamamura S.Mochida T.Akita H. Synlett 2007, 63
- 4b 
             
            Kato K.Teraguchi R.Yamamura S.Mochida T.Akita H.Peganova TA.Vologdin NV.Gusev OV. Synlett 2007, 638
- 4c 
             
            Kato K.Yamamoto Y.Akita H. Tetrahedron Lett. 2002, 43: 6587
- 4d 
             
            Kato K.Nouchi H.Ishikura K.Takaishi S.Motodate S.Tanaka H.Okudaira K.Mochida T.Nishigaki R.Shigenobu K.Akita H. Tetrahedron 2006, 62: 2545
- 5a Compound 3a:  
            Denichoux A.Ferreira F.Chemla F. Org. Lett. 2004, 6: 3509
- 5b Compound 3b:  
            Lucas S.Kazmaier U. Synlett 2006, 255
- 5c Compound 3c:  
            Yoo B.-W.Lee S.-J.Choi K.-H.Keum S.-R.Ko J.-J.Choi K.-I.Kim J.-H. Tetrahedron Lett. 2001, 42: 7287
- 5d Compound 3d: 
            Ma S.Yu S.Yin S. J. Org. Chem. 2003, 68: 8996
- 5e Compounds 3e and 3f:  
            Hashmi ASK.Ruppert TL.Knofel T.Bats JW. J. Org. Chem. 1997, 62: 7295
- 6a 
             
            Kato K.Tanaka M.Yamamoto Y.Akita H. Tetrahedron Lett. 2002, 43: 1511
- 6b 
             
            Kato K.Matsuba C.Kusakabe T.Takayama H.Yamamura S.Mochida T.Akita H.Peganova TA.Vologdin NV.Gusev OV. Tetrahedron 2006, 62: 9988
- 6c 
             
            Kato K.Tanaka M.Yamamura S.Yamamoto Y.Akita H. Tetrahedron Lett. 2003, 44: 3089
- 6d 
             
            Kusakabe T.Kato K.Takaishi S.Yamamura S.Mochida T.Akita H.Peganova TA.Vologdin NV.Gusev OV. Tetrahedron 2008, 64: 319
- 7 Au(III)-Bipyridine complex:  
            Cinellu MA.Minghetti G.Pinna MV.Stoccoro S.Zucca A.Manassero M.Sansoni M. J. Chem. Soc., Dalton Trans. 1998, 1735
- 8 
             SHELXL97. Program for the Solution of Crystal Structures
              
             
            Sheldrick GM. University of Göttingen; Germany: 1997.Reference Ris Wihthout Link
 
    