Abstract

When it comes to making 1,2-disubstituted olefins with metathesis chemistry, most synthetic chemists have taken sides. That is to say, they’ve tended to produce Z-olefins, in which the substituents are oriented to the same side of the double bond. Chemists led by Boston College’s Amir H. Hoveyda have now switched sides by developing a cross-metathesis route to E-alkenyl chlorides and fluorides. Selective synthesis of the E-isomers, in which the substituents are oriented to opposite sides of the double bond, had previously proven challenging via metathesis (Science 2016, DOI: 10.1126/science.aaf4622). The new transformation, which uses a molybdenum catalyst to swap the C=C bonds between an olefin and a simple E-dihaloalkene, uses kinetic control to guide formation of the thermodynamically less-stable E-isomer. Hoveyda’s team used the reaction to prepare derivatives of medicinally important compounds, such as the motion-sickness drug cinnarizine (shown). Alois Fürstner, a metathesis expert at the Max Planck Institute for

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