Zinc Metal-Promoted Nucleophilic Addition of Azetidin-2-ones to Aldehydes and Nitriles

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

The reactivity of in situ generated organozinc reagents of 3-alkenyl-3-bromoazetidin-2-ones with aromatic and aliphatic aldehydes to give the corresponding alcohol derivatives has been studied. The effect of solvent and Lewis acids has been explored in order to improve the reaction yields. The application of this methodology to nitriles and acyl chlorides allowed the preparation of the corresponding keto derivatives. The products of these reactions could be of interest on account of their structural similarity with the already known cholesterol adsorption inhibitors.

References

• 1a Knochel P. Millot N. Rodriguez AL. Tucker CE. Org. React.  2001,  58:  417 
  CrossrefGoogle Scholar
• 1b Knochel P. Singer RD. Chem. Rev.  1993,  93:  2117 
  CrossrefGoogle Scholar
• 2a Masuyama Y. Rec. Res. Dev. Org. Chem.  2000,  4:  373 
  Article in Thieme ConnectGoogle Scholar
• 2b Luche J.-L. Sarandeses LA. In Organozinc Reagents - A Practical Approach   Knochel P. Jones P. Oxford University Press; Oxford: 1999.  p.307-323 
  Article in Thieme ConnectGoogle Scholar
• 2c Alonso F. Yus M. Rec. Res. Dev. Org. Chem.  1997,  1:  397 
  Article in Thieme ConnectGoogle Scholar
• 2d Tagliavini E. Trombini C. Umani-Ronchi A. In Advances in Carbanion Chemistry   Vol. 2:  Snieckus V. Jai Press Inc; Greenwich: 1996.  p.111-146  
  Article in Thieme ConnectGoogle Scholar
• 2e Rathke MK. Weipert P. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Pergamon; Oxford: 1991.  p.277-299  
  Article in Thieme ConnectGoogle Scholar
• 2f Fürstner A. Synthesis  1989,  571 
  Article in Thieme ConnectGoogle Scholar
• 2g Heathcock CH. In Asymmetric Synthesis   Vol. 3:  Morrison JD. Academic Press; New York: 1984.  p.144-152  
  Article in Thieme ConnectGoogle Scholar
• 3a Clader J. Science  2004,  303:  1201 
  CrossrefGoogle Scholar
• 3b Singh GS. Mini Rev. Med. Chem.  2004,  4:  69 
  CrossrefGoogle Scholar
• 3c Wu GG. Org. Process Res. Dev.  2000,  4:  298 
  CrossrefGoogle Scholar
• 3d McKittrick BA. Ma K. Huie K. Yumibe N. Davis H. Clader JW. Czarniecki M. McPhail AT. J. Med. Chem.  1998,  41:  752 
  CrossrefGoogle Scholar
• 3e Burnett DA. Caplen MA. Davis H. Burrier RE. Clader JW. J. Med. Chem.  1994,  37:  1733 
  CrossrefGoogle Scholar
• 4a Alcaide B. Almendros P. Aragoncillo C. Rodriguez-Acebes R. J. Org. Chem.  2004,  69:  826 
  CrossrefGoogle Scholar
• 4b Alcaide B. Almendros P. Aragoncillo C. Rodriguez-Acebes R. Synthesis  2003,  1163 
  CrossrefGoogle Scholar
• 4c Alcaide B. Almendros P. Aragoncillo C. Rodriguez-Acebes R. J. Org. Chem.  2001,  66:  5208 
  CrossrefGoogle Scholar
• 4d Paquette LA. Rothhaar RR. Isaac M. Rogers LM. Rogers RD. J. Org. Chem.  1998,  63:  5463 
  CrossrefGoogle Scholar
• 4e Jayaraman M. Batista MT. Manhas MS. Bose AK. Heterocycles  1998,  49:  97 
  CrossrefGoogle Scholar
• 4f Jayaraman M. Manhas MS. Bose AK. Tetrahedron Lett.  1997,  38:  709 
  CrossrefGoogle Scholar
• 4g Palomo C. Aizpurua JM. Lopez MC. Aurrekoetxea N. Oiarbide M. Tetrahedron Lett.  1990,  31:  6425 
  CrossrefGoogle Scholar
• 5 Palomo C. Aizpurua JM. Ganboa I. Oiarbide M. Eur. J. Org. Chem.  1999,  3223 
  CrossrefGoogle Scholar
• 6a Cardillo G. Fabbroni S. Gentilucci L. Perciaccante R. Piccinelli F. Tolomelli A. Tetrahedron  2004,  60:  5031 
  Article in Thieme ConnectGoogle Scholar
• 6b Cardillo G. Fabbroni S. Gentilucci L. Perciaccante R. Tolomelli A. Tetrahedron: Asymmetry  2004,  15:  593 
  Article in Thieme ConnectGoogle Scholar
• 6c Cardillo G. De Simone A. Mingardi A. Tomasini C. Synlett  1995,  1131 
  Article in Thieme ConnectGoogle Scholar
• 7a Manhas MS. Banik BK. Mathur A. Vincent JE. Bose AK. Tetrahedron  2000,  56:  5587 
  CrossrefGoogle Scholar
• 7b Manhas MS. Ghosh M. Bose AK. J. Org. Chem.  1990,  55:  575 
  CrossrefGoogle Scholar
• 7c Zamboni R. Just G. Can. J. Chem.  1979,  57:  1945 
  CrossrefGoogle Scholar
• 7d Bose AK. Spiegelmann G. Manhas MS. Tetrahedron Lett.  1971,  3167 
  CrossrefGoogle Scholar
• 8a Bari SS. Venugopalan P. Arora R. Tetrahedron Lett.  2003,  44:  895 
  CrossrefGoogle Scholar
• 8b Kingston DGI. Chem. Commun.  2001,  867 
  CrossrefGoogle Scholar
• 8c Bandini E. Favi G. Martelli G. Panunzio M. Piersanti G. Org. Lett.  2000,  2:  1077 
  CrossrefGoogle Scholar
• 8d Kende AS. Liu K. Kaldor I. Dorey G. Koch K. J. Am. Chem. Soc.  1995,  117:  8258 
  CrossrefGoogle Scholar
• 8e Nicolaou KC. Doi WM. Guy RK. Angew. Chem., Int. Ed. Engl.  1994,  33:  15 
  CrossrefGoogle Scholar
• 8f Ojima I. Habus I. Zhao M. Zucco M. Park YH. Sun CM. Brigaud T. Tetrahedron  1992,  48:  6985 
  CrossrefGoogle Scholar
• 8g Duran F. G hosez L. Tetrahedron Lett.  1970,  11:  245 
  CrossrefGoogle Scholar
• 10a Freihammer PM. Detty MR. J. Org. Chem.  2000,  65:  7203 
  CrossrefGoogle Scholar
• 10b Durst T. Sharma MK. Gabe EJ. Lee FL. J. Org. Chem.  1990,  55:  5525 
  CrossrefGoogle Scholar
• 12a Lindstroem UM. Chem. Rev.  2002,  102:  2751 
  CrossrefGoogle Scholar
• 12b Kobayashi S. Manabe K. Acc. Chem. Res.  2002,  35:  209 
  CrossrefGoogle Scholar
• 12c Fringuelli F. Piermatti O. Pizzo F. Vaccaro L. Eur. J. Org. Chem.  2001,  3:  439 
  CrossrefGoogle Scholar
• 12d Dias LC. Curr. Org. Chem.  2000,  4:  305 
  CrossrefGoogle Scholar
• 12e Laszlo P. Teston M. J. Am. Chem. Soc.  1990,  112:  8750 
  CrossrefGoogle Scholar
• 13a Kobayashi S. Busujima T. Nagayama S. Chem. Eur. J.  2000,  6:  3491 
  CrossrefGoogle Scholar
• 13b Ferraris D. Drury WJ. Cox C. Lectka T. J. Org. Chem.  1998,  63:  4568 
  CrossrefGoogle Scholar
• 13c Pearson RG. J. Am. Chem. Soc.  1963,  85:  3533 
  CrossrefGoogle Scholar
• 14a Dilman AD. Ioffe SL. Chem. Rev.  2003,  103:  733 
  CrossrefGoogle Scholar
• 14b Bongini A. Cardillo G. Mingardi A. Tomasini C. Tetrahedron: Asymmetry  1996,  7:  1457 
  CrossrefGoogle Scholar
• 14c Lipshutz BH. Dimock SH. James B. J. Am. Chem. Soc.  1993,  115:  9283 
  CrossrefGoogle Scholar
• 14d Lipshutz BH. James B. Tetrahedron Lett.  1993,  34:  6689 
  CrossrefGoogle Scholar
• 15 Cainelli G. Cardillo G. Orena M. Sandri S. J. Am. Chem. Soc.  1976,  98:  6737 
  CrossrefGoogle Scholar
• 16a Iwai T. Ito T. Mizuno T. Ishino Y. Tetrahedron Lett.  2004,  45:  1083 
  CrossrefGoogle Scholar
• 16b Lee AS.-Y. Lin L.-S. Tetrahedron Lett.  2000,  41:  8803 
  CrossrefGoogle Scholar

The reactions were performed on racemic mixtures. For the sake of simplicity only one enantiomer has been reported in the schemes.

Detailed X-ray data for 3a and 3b are reported in the experimental section. CCDC number for 3a is 245012, CCDC number for 3b is 245013.