Isophthalic Acid-Derived Dicarbothioamides as Novel Metal-Free Catalysts in Hydrogen Bond-Promoted Reactions
Articolo
Data di Pubblicazione:
2009
Citazione:
Isophthalic Acid-Derived Dicarbothioamides as Novel Metal-Free Catalysts in Hydrogen Bond-Promoted Reactions / S. Guizzetti, M. Benaglia, A. Puglisi, L. Raimondi. - In: SYNTHETIC COMMUNICATIONS. - ISSN 0039-7911. - 39:20(2009), pp. 3731-3742. [10.1080/00397910902838847]
Abstract:
The synthesis of N,N'-diaryl-1,3-benzene-dicarbothioamides was accomplished in only two steps with good yields, and their ability to act as hydrogen-bond donors in Diels-Alder reactions was evaluated. These new organocatalysts were indeed able to promote the cycloaddition of cyclopentadiene to ,-unsaturated aldehydes. In the attempt to control the absolute stereochemistry of the reaction, chiral catalysts were also prepared by simple condensation of isophthalic acid and -amino acid derivatives. Molecular mechanics calculations were performed to elucidate the mode of action of these metal-free catalytic systems and to find a rationale for the achieved enantioselectivity
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
C-C bond formation; Carbothioamides; Cycloaddition; Hydrogen bond; Organocatalysis
Elenco autori:
S. Guizzetti, M. Benaglia, A. Puglisi, L. Raimondi
Link alla scheda completa: