Stereoselective Reaction of Acylic Alkenes

Epoxidation of Z-Allyl Silanes

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Click the reaction arrow in sequence to view the 3D models and animations respectively

Examine the interactive energy diagram for the starting Z-allyl silane.

Allylic 1,3-strain ensures that the lowest energy conformation has the hydrogen on the allylic centre eclipsing the Z-methyl group. The peroxyformic acid approaches the face that is not hindered by the trimethylsilyl group to produce the anti epoxide.

R. W. Hoffmann, Chem. Rev., 1989, 89, 1841–1860.