PAPER: β-olefination of 2-alkynoates leading to trisubstituted 1,3-dienes

Jacobsen M. J., Funder E. D., Cramer J. R., Gothelf K. V.

Org. Lett. 2011, 13, 3418–3421, doi: 10.1021/ol2011677

Danish National Research Foundation: Centre for DNA Nanotechnology (CDNA) at Department of Chemistry and iNANO, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark


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 δ-position. Proof of concept is shown for the generation of a β,γ-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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