In a two-step one-pot procedure the allylic alcohol 1 can be converted diastereoselectively into the epoxy diols (S*,R*,S*)- and (S*,R*,R*)-3 (d.r. 95: 5), simply by adding a catalytic amount of Ti(OiPr)4, to a photooxygenated solution of the allylic alcohol 1, and stopping the reaction after the complete conversion of the hydroperoxide (S*,S*)-2, which is present in addition to the R*,S* isomer. TTP tetraphenylporphyrin.
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Adam et al. (1993) studied this question.
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