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        Synthesis  2007(20): 3195-3200  
DOI: 10.1055/s-2007-990781
   DOI: 10.1055/s-2007-990781
PAPER
© Georg Thieme Verlag Stuttgart · New YorkN-Heterocyclic Carbene Catalyzed Reaction of Enals and Diaryl-1,2 diones via Homoenolate: Synthesis of 4,5,5-Trisubstituted γ-Butyrolactones
Further Information
            
               
                  
                        
                              Received
                              23 May 2007 
                      
Publication Date:
21 September 2007 (online)
            
         
      
   Publication History
Publication Date:
21 September 2007 (online)

Abstract
Nucleophilic heterocyclic carbene (NHC)-catalyzed annulation of enals proceeds with variety of 1,2-dicarbonyl compounds, leading to the formation of 4,4,5-trisubstituted γ-butyrolactones.
Key words
lactones - homoenolate - N-heterocyclic carbene - benzil - thenil - furil
- 1 
             
            Nickon A.Lambert JL. J. Am. Chem. Soc. 1962, 84: 4604Reference Ris Wihthout Link
- For reviews on homoenolate anion and their equivalents, see:
- 2a 
             
            Kuwajima I.Nakamura E. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I. Pergamon; New York: 1991. p.441 ; and references cited therein
- 2b 
             
            Lee VJ. In Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I. Pergamon; New York: 1991. p.117 ; and references cited therein
- 2c 
             
            Werstiuk NH. Tetrahedron 1983, 39: 205
- 2d 
             
            Stowell JC. Chem. Rev. 1984, 84: 409
- 3 
             
            Bal AS.Marfat A.Helquist P. J. Org. Chem. 1982, 47: 5045
- 4 
             
            Lombaert SD.Lesur B.Ghosez L. Tetrahedron Lett. 1982, 23: 4251
- 5 
             
            Nakamura E.Aoki S.Sekiya K.Oshino H.Kuwajima I. J. Am. Chem. Soc. 1987, 109: 8056
- Selected references:
- 6a 
             
            Binns MR.Haynes RK. J. Org. Chem. 1981, 46: 3790
- 6b 
             
            Hirama M. Tetrahedron Lett. 1981, 22: 1905
- 6c 
             
            Krams GA.Fraizier K. Synth. Commun. 1978, 8: 483
- 6d 
             
            Sanchez IH.Aguilar AM. Synthesis 1981, 55
- 6e 
             
            Binns MR.Haynes RK.Katsifis AG.Schober PA.Vonwiller SC.Hambley TW. J. Am. Chem. Soc. 1988, 110: 5411
- 6f 
             
            Hua DH.Venkataraman S.Ostrander RA.Gurudas SZ.McCann PJ.Coulter MJ.Xu MR. J. Org. Chem. 1988, 53: 507 ; and references cited therein
- 6g 
             
            Ahlbrecht H.Dietz M.Weber L. Synthesis 1987, 251
- For chiral homoenolates, see :
- 7a 
             
            Özlügedik M.Kristensen J.Wibbeling B.Fröhlich R.Hoppe D. Eur. J. Org. Chem. 2002, 414
- For recent examples, see:
- 7b 
             
            Seppi M.Kalkofen R.Reupohl J.Fröhlich R.Hoppe D. Angew. Chem. Int. Ed. 2004, 43: 1423
- 7c 
             
            Reuber J.Fröhlich R.Hoppe D. Org. Lett. 2004, 6: 783
- 8a 
             
            Sohn SS.Rosen EL.Bode JW. J. Am. Chem. Soc. 2004, 126: 14370
- 8b 
             
            Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205
- 8c 
             
            Chan A.Scheidt KA. Org. Lett. 2005, 7: 905
- 8d 
             
            He M.Bode JW. Org. Lett. 2005, 7: 3131
- 8e 
             
            Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506
- 8f 
             
            Burstein C.Tschan S.Xie X.Glorius F. Synthesis 2006, 2418
- 9 
             
            Breslow R. J. Am. Chem. Soc. 1958, 80: 3719Reference Ris Wihthout Link
- For reviews, see:
- 10a 
             
            Nair V.Bindu S.Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130Reference Ris Wihthout Link
- 10b 
             
            Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534Reference Ris Wihthout Link
- 10c 
             
            Marion N.Diez-Gonzalez S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988Reference Ris Wihthout Link
- 11a 
             
            Nair V.Pillai AN.Menon RS.Suresh E. Org. Lett. 2005, 7: 1189
- 11b 
             
            Nair V.Biju AT.Abhilash KG.Menon RS.Suresh E. Org. Lett. 2005, 7: 2121
- 12 
             
            Nair V.Vellalath S.Poonoth M.Mohan R.Suresh E. Org. Lett. 2006, 8: 507
- 14a 
             
            Chatani N.Tobisu M.Asaumi T.Fukumoto Y.Murai SW. J. Am. Chem. Soc. 1999, 121: 7160
- 14b 
             
            Tobisu M.Chatani N.Asaumi T.Amako K.Ie Y.Fukumoto Y.Murai SW. J. Am. Chem. Soc. 2000, 122: 12663
- 14c 
             
            Ye W.Cai G.Zhuang Z.Jia X.Zhai H. Org. Lett. 2005, 7: 3769
- For reviews, see:
- 15a 
             
            Seitz M.Reiser O. Curr. Opin. Chem. Biol. 2005, 9: 285
- 15b 
             
            Hoffmann HMR.Rabe J. Angew. Chem., Int. Ed. Engl. 1985, 24: 94
- 15c 
             
            Ito M. Pure Appl. Chem. 1991, 63: 13
References
CCDC 280173 (4a) and 626910 (11a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
 
    