Abstract
The gold(I)-catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)-1,4-disubstituted 1,3-butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user-friendly procedure. Reaction of acetylene with 1,5-dienes gives rise stereoselectively to tricyclo[5.1.0.02,4]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.
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Scharnagel, D., Escofet, I., Armengol-Relats, H., de Orbe, M. E., Korber, J. N., & Echavarren, A. M. (2020). Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step. Angewandte Chemie - International Edition, 59(12), 4888–4891. https://doi.org/10.1002/anie.201915895
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