Enyne Metathesis

By: William Sommer, Aldrich ChemFiles 2009, 9.6, 7.

Aldrich ChemFiles 2009, 9.6, 7.

Enyne metathesis has emerged as a powerful method for the synthesis of conjugated dienes.1 Botta and coworkers utilized a similar approach, where the olefin was replaced with an enol ether. Reaction between the alkyne and the enol ether generated the ß-substituted crotonaldehydes in good yields. The reaction is conducted in the presence of the Grubbs catalyst (2nd Generation), an aqueous solution of CuSO4, and under microwave conditions. Irradiation under microwave conditions (3 X 10 minutes) is followed by the addition of iodine to provide the desired crotonaldehydes in good yields (Scheme 4).2

Scheme 4

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  1. Diver, S. T. et al. Chem. Rev. 2004, 104, 1317.
  2. Castagnolo, D. et al. J. Org. Chem. 2009, 74, 3172.

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