Journal
ORGANIC LETTERS
Volume 13, Issue 13, Pages 3418-3421Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2011677
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Funding
- Danish National Research Foundation through Centre for DNA Nanotechnology
- Sino-Danish Centre for Molecular Self-assembly on Surfaces
- Centre of Functionally Integrative Neuroscience
- OChem graduate school
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A phosphine-mediated olefination of 2-alkynoates with aldehydes forming 1,3-dienes with high E-selectivity and up to 88% yield is described. Reaction conditions are optimized and reactions are demonstrated for,various aryl, alkyl, and alkenyl aldehydes and for ethyl 2-alkynoates with different substituents in the delta-position. Proof of concept is shown for the generation of a beta,gamma-unsaturated lactone by intramolecular olefination, and furthermore the use of the generated 1,3-dienes in the Diels-Alder reaction has been demonstrated.
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