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Tridentate β‐Hydroperoxy Alcohols as Novel Oxygen Donors for the Titanium‐Catalyzed Epoxidation of γ,δ‐Unsaturated α,β‐Diols: A Direct Diastereoselective Synthesis of Epoxy Diols

1994; Wiley; Volume: 33; Issue: 10 Linguagem: Inglês

10.1002/anie.199411071

1521-3773

Waldemar Adam, Karl Peters, Michael Renz,

Polyoxometalates: Synthesis and Applications

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.