Zincke Aldehyde

Zincke Aldehyde

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  • General Characteristics

Upon nucleophilic attack by secondary amines, 1-(2,4-dinitrophenyl)pyridinium chloride (the Zincke salt) opens up to give 5-aminopenta-2,4-dienal (the Zincke aldehyde).

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  • Reaction Mechanism

zincke_aldehyde_3.gif

  • Examples

The aminodienal prepared using the Zincke salt served as a key intermediate in the synthesis of a complex indole alkaloid.[1]

zincke_aldehyde_2.gif

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  • References

[1] (a) Martin, D.B.C.; Vanderwal, C.D. J. Am. Chem. Soc. 2009, 131 , 3472. doi:10.1021/ja900640v
(b) Martin, D.B.C.; Vanderwal, C.D. Chem. Sci. 20112, 649. doi:10.1039/C1SC00009H

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