Lood, K.; Tikk, T.; Krüger, M.; Schmidt, B.
Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol
J. Org. Chem. 2022, 87, 3079-3088
DOI: 10.1021/acs.joc.1c02851
Xylochemicals are chemicals derived from wood-based renewables, e. g. lignin. A number of naturally occurring isopropenylbenzenes, e. g. isoeugenol, trans-anethole and α-asarone, were found to be effective substrates for olefin cross metathesis reactions with crotonaldehyde to furnish valuable oxygenated cinnamaldehydes. Surprisingly, the cross metathesis reactions proceed more efficiently with crotonaldehyde than with the sterically less hindered acrolein, which we attribute to methylene capping of the propagating catalytically active Ru-carbene species. The method was applied to the synthesis of the natural product 7-methoxywutaifuranal, which was synthesized through a one-pot RCM-CM-sequence.
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