Organic Chemistry Portal



Julia-Kocienski Reaction-Based 1,3-Diene Synthesis: Aldehyde-Dependent (E,E/E,Z)-Selectivity

François Billard, Raphaël Robiette and Jiří Pospíšil*

*Institute of Condensed Matter and Nanosciences−Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium, Email:

F. Billard, R. Robiette, J. Pospíšil, J. Org. Chem., 2012, 77, 6358-6364.

DOI: 10.1021/jo300929a (free Supporting Information)

see article for more reactions


A new modification of Julia-Kocienski olefination reaction based on the use of cation-specific chelating agents yields 1,3-dienes with predictable (E/Z)-selectivity. The influence of the aldehyde structure on the (E/Z) selectivity is discussed.

see article for more examples

Efficient and Stereoselective Synthesis of Allylic Ethers and Alcohols

J. Pospisil, I. E. Marko, Org. Lett., 2006, 8, 5983-5986.

Key Words

Julia-Kocienski Reaction, 1,3-Dienes

ID: J42-Y2012-2390