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Gold-Catalyzed Synthesis of Furans and Furanones from Sulfur Ylides

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58636

Huang,  Xueliang
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58879

Peng,  Bo
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58783

Luparia,  Marco
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132839

Gomes,  Luis F. R.
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58809

Maulide,  Nuno
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Huang, X., Peng, B., Luparia, M., Gomes, L. F. R., Veiros, L., & Maulide, N. (2012). Gold-Catalyzed Synthesis of Furans and Furanones from Sulfur Ylides. Angewandte Chemie International Edition: a journal of the Gesellschaft Deutscher Chemiker, 51(35), 8886-8890. doi:10.1002/anie.201203637.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0010-20EC-6
Abstract
A golden switch: Doubly stabilized sulfonium ylides can be coupled with alkynes in a gold-catalyzed synthesis of heterocycles. This method hinges on a switch in the reactivity of the sulfur ylide resulting from the simple modification of the electron-withdrawing moieties and leads to either furans or furanones bearing a quaternary center (see scheme).