High yields and only traces of side products are possible in the synthesis of epoxides by oxidation of alkenes when the urea/hydrogen peroxide adduct (UHP) is used as the oxygen donor in the methyltrioxorhenium(VII)-catalyzed reaction (see below). Chiral allylic alcohols with 1,3-strain were employed as stereochemical probes; the high threo diastereoselectivities obtained allow important mechanistic insights into the oxygen transfer process.
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Adam et al. (1996) studied this question.
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