Mono- and Bis-Acrolein Derivatives by Reliable and Efficient One-Step Methylenation of Aldehyde Precursors

 

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Abstract

A series of aldehydes carrying different functional groups was transformed directly into the α-methylene derivatives. Dialdehydes behaved comparably at both active sites. When keto aldehydes are involved, excellent levels of chemoselectivity are observed, with the ketone substructures exhibiting no sign of reactivity.

References

• 1a Blicke FF. Org. React.  1942,  1:  303 
  Article in Thieme ConnectGoogle Scholar
• 1b Hellmann H. Opitz G. Angew. Chem.  1956,  68:  265 
  Article in Thieme ConnectGoogle Scholar
• 1c Reichert B. Die Mannich Reaktion   Springer-Verlag; Berlin: 1959. 
  Article in Thieme ConnectGoogle Scholar
• 1d Hellman H. Opitz G. α-Aminoalkylierung   Verlag Chemie, Weinheim; Germany: 1960. 
  Article in Thieme ConnectGoogle Scholar
• 1e Tramontini M. Synthesis  1973,  703 
  Article in Thieme ConnectGoogle Scholar
• 2 Kinast G. Tietze L.-F. Angew. Chem., Int. Ed. Engl.  1976,  15:  239 
  CrossrefGoogle Scholar
• 3 White JD. Amedio JC. Hrnciar P. Lee NC. Ohira S. Yokochi AFT. Chem. Commun.  1998,  603 
  CrossrefGoogle Scholar
• 4 Paquette LA. Hofferberth JE. J. Org. Chem.  2003,  68:  2265 
  Google Scholar
• 5a Gras J.-L. Tetrahedron Lett.  1978,  19:  2111 
  CrossrefGoogle Scholar
• 5b Gras J.-L. Tetrahedron Lett.  1978,  19:  2955 
  CrossrefGoogle Scholar
• 6a Farberov MI. Mironov GS. Dokl. Akad. Nauk SSSR  1963,  148:  1095 ; Chem. Abstr. 1963, 59, 5062
  Google Scholar
• 6b Mironov GS. Farberov MI. Korshunov MA. Uch. Zap. Yaroslavsk. Tekhn. Inst.  1962,  33 ; Chem. Abstr. 1964, 61, 568
  Google Scholar
• 7 Takano S. Inomata K. Samizu K. Tomita S. Yanase M. Suzuki M. Iwabuchi Y. Sugihara T. Ogasawara K. Chem. Lett.  1989,  1283 
  Google Scholar
• 8 For a recent synthetic application of such products, consult: Groth U. Jung M. Vogel T. Synlett  2004,  1054 
  Article in Thieme ConnectGoogle Scholar