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Journal Article

Direct Domino Synthesis of Azido-Dienoic Acids: Potential Linker Units

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/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/persons58809

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

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Supplementary Material (public)

sup_st-2013-d0143-l_10-1055_s-0033-1338452.pdf
(Supplementary material), 3MB

Citation

Souris, C., Frébault, F., Audisio, D., Farès, C., & Maulide, N. (2013). Direct Domino Synthesis of Azido-Dienoic Acids: Potential Linker Units. Synlett, 24(10), 1286-1290. doi:10.1055/s-0033-1338452.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-CA0C-C
Abstract
We report an atom-economical domino synthesis of functionalized and stereodefined dienes. This method hinges on an allylic alkylation–electrocyclic ring-opening sequence and allows direct access to doubly vinylogous azido-dienoic acids bearing challenging substitution patterns. This class of compounds re­presents useful linkers in chemical biology by virtue of the ortho­gonality between the azido and carboxylic acid moieties.