An attractive direct route to epoxy diols 2 relies on the Ti-catalyzed epoxidation of enediols 1 with 2-hydroperoxy-2-phenylpropan-l-ol. Under conventional Sharpless epoxidation conditions (bidentate tBuOOH) diols 1 react very sluggishly; however, with the new tridentate oxygen donor these same diols undergo smooth reaction to give products 2 in high diastereoselectivity and without the use of protecting groups.
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Adam et al. (1994) studied this question.
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