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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.
Examine the interactive energy diagram for the starting Z-allyl silane.
R. W. Hoffmann, Chem. Rev., 1989, 89, 1841–1860.
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