PDF herunterladen
Synthesis 2010(6): 1053-1057  
DOI: 10.1055/s-0029-1217135
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Mild and High-Yielding Synthesis of β-Keto Esters and β-Ketoamides

Vellaisamy Sridharan, Miriam Ruiz, J. Carlos Menéndez*
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
Fax: +34(91)3941822; e-Mail: josecm@farm.ucm.es;
Weitere Informationen

Publikationsverlauf

Received 30 June 2009
Publikationsdatum:
20. November 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and β-keto esters and β-ketoamides were normally obtained in quantitative yields.

Key words

acetoacetylation - chiral auxiliaries - dicarbonyl compounds - esters - amides

    References

  • 1a For an extensive review on the synthetic applications of β-keto esters, see: Benetti S. Romagnoli R. De Risi C. Spalluto G. Zanirato V. Chem. Rev.  1995,  95:  1065 
    Suche in Google Scholar
  • 1b For a review of the use of β-dicarbonyl compounds in multicomponent reactions, see: Simon C. Constantieux T. Rodriguez J. Eur. J. Org. Chem.  2004,  4957 
  • For selected recent examples, see:
  • 2a Ducatti DRB. Massi A. Noseda MD. Duarte MER. Dondoni A. Org. Biomol. Chem.  2009,  7:  1980 
    Suche in Google Scholar
  • 2b Debache A. Boulcina R. Belfaitah A. Rhouati S. Carboni B. Synlett  2008,  509 
  • 2c Chitra S. Pandiarajan K. Tetrahedron Lett.  2009,  50:  2222 
    Suche in Google Scholar
  • 2d Singh OM. Devi NS. J. Org. Chem.  2009,  74:  3141 
    Suche in Google Scholar
  • 2e Velezheva VS. Sokolov AI. Kornienko AG. Lyssenko KA. Nelyubina YV. Godovikov IA. Peregudov AS. Mironov AF. Tetrahedron Lett.  2008,  49:  7106 
    Suche in Google Scholar
  • 2f Wang H.-M. Hou R.-S. Cheng H.-T. Chen L.-C. Heterocycles  2009,  78:  487 
    Suche in Google Scholar
  • 2g Thomae D. Perspicace E. Hesse S. Kirsch G. Seck P. Tetrahedron  2008,  64:  9309 
    Suche in Google Scholar
  • 3 Sridharan V. Menéndez JC. Org. Lett.  2008,  10:  4303 
    CrossrefSuche in Google Scholar
  • For selected examples involving the reactions of β-keto esters attached to chiral auxiliaries, see:
  • 4a Xu H.-W. Li G.-Y. Wong M.-K. Che C.-M. Org. Lett.  2005,  7:  5349 
    Suche in Google Scholar
  • 4b Frantz R. Hintermann L. Perseghini M. Broggini D. Togni A. Org. Lett.  2003,  5:  1709 
    Suche in Google Scholar
  • 4c Myers AG. Tom NJ. Fraley ME. Cohen SB. Madar DJ. J. Am. Chem. Soc.  1997,  119:  6072 
    Suche in Google Scholar
  • For selected transesterification methodologies, see:
  • 5a Gilbert JC. Kelly TA. J. Org. Chem.  1988,  53:  449 
    Suche in Google Scholar
  • 5b Chavan SP. Kale RR. Shivashankar K. Chandake SI. Benjamin SB. Synthesis  2003,  2695 
  • 5c Ribeiro RS. de Souza ROMA. Vasconcellos MLAA. Oliveira BL. Ferreira LC. Aguiar LCS. Synthesis  2007,  61 
  • 5d Kondaiah GCM. Reddy LA. Babu KS. Gurav VM. Huge KG. Bandichhor R. Reddy PP. Bhattacharya A. Anand RV. Tetrahedron Lett.  2008,  49:  106 
    Suche in Google Scholar
  • 6 Taber DF. Saleh SA. Korsmeyer RW. J. Org. Chem.  1980,  45:  4699 
    CrossrefSuche in Google Scholar
  • 7 Clemens RJ. Hyatt JA. J. Org. Chem.  1985,  50:  2431 
    CrossrefSuche in Google Scholar
  • 8 Marco JL. Martín N. Martínez-Grau A. Seoane C. Albert A. Cano FH. Tetrahedron  1994,  50:  3509 
    CrossrefSuche in Google Scholar
  • 9 López-Alvarado P. Avendaño C. Menéndez JC. Synth. Commun.  1992,  22:  2329 
    CrossrefSuche in Google Scholar
  • 10 For a review, see: Sato M. Sunami S. Kaneko C. Heterocycles  1996,  42:  861 
    CrossrefSuche in Google Scholar
  • For recent examples, see:
  • 11a Sridharan V. Perumal P. T. Avendaño C. Menéndez JC. Tetrahedron  2007,  63:  4407 
    Suche in Google Scholar
  • 11b Sridharan V. Avendaño C. Menéndez JC. Tetrahedron  2009,  65:  2087 
    Suche in Google Scholar
  • 11c Maiti S. Menéndez JC. Synlett  2009,  2249 
  • 11d Sridharan V. Ribelles P. Ramos MT. Menéndez JC. J. Org. Chem.  2009,  74:  5715 
    Suche in Google Scholar
  • 11e Sridharan V. Maiti S. Menéndez JC. Chem. Eur. J.  2009,  15:  4565 
    Suche in Google Scholar
  • 12 Bader AR. Commings LO. Vogel HA. J. Am. Chem. Soc.  1951,  73:  4195 
    CrossrefSuche in Google Scholar
  • 13 Mukaiyama T. Makoto T. Nohira H. Hisashi T. J. Org. Chem.  1961,  26:  4381 
    CrossrefSuche in Google Scholar
  • 14 Beger J. Thielemann C. J. Prakt. Chem.  1981,  323:  337 
    CrossrefSuche in Google Scholar