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An Atom-Economical and Stereoselective Domino Synthesis of Functionalised Dienes

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons59007

Souris,  Caroline
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/persons58553

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58402

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58537

Farès,  Christophe
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58578

Goddard,  Richard
Service Department Lehmann (EMR), 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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Supplementary Material (public)

chem_201300776_sm_miscellaneous_information.pdf
(Supplementary material), 8MB

Citation

Souris, C., Luparia, M., Frébault, F., Audisio, D., Farès, C., Goddard, R., et al. (2013). An Atom-Economical and Stereoselective Domino Synthesis of Functionalised Dienes. Chemistry - A European Journal, 19(21), 6566-6570. doi:10.1002/chem.201300776.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-CA09-1
Abstract
Open sesame: A direct synthesis of functionalised and stereodefined dienes, relying on a domino allylic alkylation/electrocyclic ring-opening sequence, is reported. This method allows concise access to doubly vinylogous esters. A further systematic study of ring-opening rates of carbon-substituted cyclobutenes allowed the design of substrates amenable to sequential pericyclic reactions.