Abstract
Coupling reactions of epoxide linked to a secondary oxygen group with Gilman reagents were examined. The regiochemical direction depended on whether there is TMS or MOM as a protective group of the secondary alcohol. anti-Epoxy alcohol 6 tended to react with Me2CuLi at the C4 position to generate 1,2-diol 22 as a major component. Epoxide 7 linked to a trimethylsilyloxy group displayed selective formation of 1,3-diol 18. On the other hand, the reactions of syn-epoxy alcohol 12 and the corresponding TMS ether 13 resulted in the selective formation of 1,2-diol 25.
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