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
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]
Isophthalic Acid-Derived Dicarbothioamides as Novel Metal-Free Catalysts in Hydrogen Bond-Promoted Reactions
S. GuizzettiPrimo
;M. BenagliaSecondo
;A. PuglisiPenultimo
;L. RaimondiUltimo
2009
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 enantioselectivityFile | Dimensione | Formato | |
---|---|---|---|
SynthComm_2009_3731.pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
382.41 kB
Formato
Adobe PDF
|
382.41 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.