期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 12, 页码 4888-4891出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915895
关键词
acetylene; cyclopropanation; gold catalysis; total synthesis
资金
- Agencia Estatal de Investigacion (AEI)/FEDER, UE [CTQ2016-75960-P]
- European Research Council [835080]
- AGAUR [2017 SGR 1257]
- CERCA Program/Generalitat de Catalunya
- Deutsche Forschungsgemeinschaft
- European Research Council (ERC) [835080] Funding Source: European Research Council (ERC)
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[5.1.0.0(2,4)]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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