Dr. Rylan Lundgren has developed a process for formate-mediated production of Z-olefins (also referred to as cis-alkenes) in the presence of a rhodium-based catalyst. The process is highly selective for the Z-olefin product over the E-olefin (or trans-alkene) and accommodates a wide variety of substitutions at the R position in Figure 1 above. This process overcomes the difficult problem in synthetic chemistry of selective catalysis of the thermodynamically disfavored Z-olefins.
The Z-olefin unit is found in a variety of commercially-relevant laboratory and industrial compounds, including drug molecules, agrochemicals, and fine chemicals and fragrances. Synthetic methods typically produce a mixture of Z- and E-olefins, usually weighted towards the E-olefins. Although purifying the two Z- and E- forms are possible, it is often difficult and time consuming. Alkyne semi-hydrogenation and olefin metathesis are currently the most accepted method for selectively generating Z-olefins, but our method provides several advantages:
⦁ does not require high pressures of H2 gas;
⦁ can be carefully controlled to prevent over-reduction of the product;
⦁ tolerates a diverse number of alternative reducible functional groups, which are not affected; this allows the process to be applied to 1,3-dienes in mixtures with other species or on structurally complex bioactive molecules
Technology Management Group
TEC Edmonton – University of Alberta