Synthesis 2005(14): 2335-2340  
DOI: 10.1055/s-2005-869985
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Entry to Bicyclic β-Lactams via Free Radical Cyclization of 2-Azetidinone-Tethered Bromohomoallylic Alcohols

Benito Alcaide*a, Pedro Almendros*b, Raquel Rodríguez-Acebesa
a Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040-Madrid, Spain
Fax: +34(91)3944103; e-Mail: alcaideb@quim.ucm.es;
b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain
Fax: +34(91)564853; e-Mail: iqoa392@iqog.csic.es;
Further Information

Publication History

Received 16 February 2005
Publication Date:
27 June 2005 (online)

Abstract

Triphenyltin hydride-promoted reaction of β-lactam-tethered bromodienes gave six-, seven-, or eight-membered bicyclic ring structures through intramolecular free radical cyclization. The cyclization precursors were synthesized by stereoselective tin-mediated carbonyl bromoallylation of 4-oxoazetidine-2-carbaldehydes in an aqueous environment.

    References

  • 1a Hot Topic: β-Lactams: Synthesis, Stereochemistry, Synthons, and Biological Evaluation: Banik BK. Curr. Med. Chem.  2004,  11:  issue 14 
  • 1b Walsh C. Antibiotics: Actions Origins Resistance   ASM Press; Washington DC: 2003. 
  • 1c Mascaretti OA. Bacteria versus Antibacterial Agents   ASM Press; Washington DC: 2003. 
  • 1d Niccolai D. Tarsi L. Thomas RJ. Chem. Commun.  1997,  2333 
  • 1e The Chemistry of β-Lactams   Page MI. Chapman and Hall; London: 1992. 
  • For reviews on allylmetal additions see:
  • 2a Kennedy JWJ. Hall DG. Angew. Chem. Int. Ed.  2003,  42:  4732 
  • 2b Denmark SE. Fu J. Chem. Rev.  2003,  103:  2763 
  • 2c Roush WR. Chemler CR. In Modern Carbonyl Chemistry   Otera J. Wiley-VCH; Weinheim: 2000.  Chap. 11.
  • 2d Denmark SE. Almstead NG. In Modern Carbonyl Chemistry   Otera J. Wiley-VCH; Weinheim: 2000.  Chap. 10.
  • 2e Thomas EJ. Chem. Commun.  1997,  411 
  • 2f Marshall JA. Chem. Rev.  1996,  96:  31 
  • 2g Yamamoto Y. Asao N. Chem. Rev.  1993,  93:  2207 
  • 3a Trost BM. Coppola BP. J. Am. Chem. Soc.  1982,  104:  6879 
  • 3b Mandai T. Nokami J. Yano T. Yoshinaga Y. Otera J. J. Org. Chem.  1984,  49:  172 
  • 3c Kurosu M. Lin M.-H. Kishi Y. J. Am. Chem. Soc.  2004,  126:  12248 
  • See for example:
  • 4a Trost BM. Corte JR. Gudiksen MS. Angew. Chem. Int. Ed.  1999,  38:  3662 
  • 4b Crimmins MT. She J. J. Am. Chem. Soc.  2004,  126:  12790 
  • See for instance:
  • 5a Alcaide B. Almendros P. Alonso JM. J. Org. Chem.  2004,  69:  993 
  • 5b Alcaide B. Almendros P. Redondo MC. Org. Lett.  2004,  6:  1765 
  • 5c Alcaide B. Almendros P. Aragoncillo C. Rodríguez-Acebes R. J. Org. Chem.  2004,  69:  826 
  • 5d Alcaide B. Almendros P. Alonso JM. Chem.-Eur. J.  2003,  9:  5793 
  • 5e Alcaide B. Almendros P. Aragoncillo C. Org. Lett.  2003,  5:  3795 
  • 5f Alcaide B. Almendros P. Alonso JM. Aly MF. Chem.-Eur. J.  2003,  9:  3415 
  • 6a Alcaide B. Martín-Cantalejo Y. Plumet J. Rodríguez-López J. Sierra MA. Tetrahedron Lett.  1991,  32:  803 
  • 6b Alcaide B. Martín-Cantalejo Y. Pérez-Castells J. Rodríguez-López J. Sierra MA. Monge A. Pérez-García V. J. Org. Chem.  1992,  57:  5921 
  • 7 Alcaide B. Almendros P. Rodríguez-Acebes R. J. Org. Chem.  2005,  71:  2713 
  • 8 Stork G. Baine NH. J. Am. Chem. Soc.  1982,  104:  2321 
  • 9a Zard SZ. Radicals Reactions in Organic Synthesis   Oxford University Press Inc.; New York: 2003. 
  • 9b Giese B. Kopping B. Göbel T. Dickhaut J. Thoma G. Kulicke KJ. Trach F. Org. React.  1996,  48:  301 
  • 9c Motherwell WB. Crich D. Free Radical Chain Reactions in Organic Synthesis   Academic Press; London: 1992. 
  • 9d Jasperse CP. Curran DP. Fevig TL. Chem. Rev.  1991,  91:  1237 
  • 9e Curran DP. Synthesis  1988,  417 
  • 9f Curran DP. Synthesis  1988,  489 
  • The synthesis of medium-sized rings has usually been hampered by entropic/enthalpic factors and transannular interactions between the methylene groups. For reviews see:
  • 10a Galli L. Mandolini L. Eur. J. Org. Chem.  2000,  3117 
  • 10b Illuminati G. Mandolini L. Acc. Chem. Res.  1981,  14:  95 
  • The only available examples are:
  • 11a Deshmukh ARAS. Jayanthi A. Thiagarajan K. Puranik VG. Bhawal BM. Synthesis  2004,  2965 
  • 11b Jayanthi A. Puranik VG. Deshmukh ARAS. Synlett  2004,  1249 
  • 11c Alcaide B. Almendros P. Pardo C. Rodríguez-Ranera C. Rodríguez-Vicente V. J. Org. Chem.  2003,  68:  3106 
  • 11d Alcaide B. Almendros P. Aragoncillo C. J. Org. Chem.  2001,  66:  1612 
  • 11e Penfold DJ. Pike K. Genge A. Anson M. Kitteringham J. Kilburn JD. Tetrahedron Lett.  2000,  41:  10347 
  • 11f Knight J. Parsons PJ. J. Chem. Soc., Perkin Trans. 1  1987,  1237 
  • 11g Knight J. Parsons PJ. Southgate R. J. Chem. Soc., Chem. Commun.  1986,  78