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An Atom-Economical and Stereoselective Domino Synthesis of Functionalised Dienes

MPS-Authors
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Souris,  Caroline
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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

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

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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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: https://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.