Reaction Mechanism
The initial steps are straightforward. The phenyl sulfone anion (2) reacts with an aldehyde to form the alkoxide 3. The alkoxide is functionalized with R3-X to give the stable intermediate 4. The exact mechanism of the sodium amalgam reduction is unknown but has been shown to proceed through a vinylic radical species (5). Protonation of the vinylic radical gives the desired product (6).
The stereochemistry of the alkene (6) is independent of the stereochemistry of the sulfone intermediate 4. It is thought that the radical intermediates are able to equilibrate so that the more thermodynamically stable trans-olefin is produced most often.
Read more about this topic: Julia Olefination
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