Chiral β-oxidofunctionalised organolithium compounds from epoxides: EPC-synthesis of 1,3-diols

Article abstract of DOI:10.1016/0957-4166(95)00249-O

The reductive opening of (S)-propylene oxide (1) with lithium powder and a catalytic amount of DTBB (5 mol %) in THF -78°C followed by treatment with different carbonyl compounds [Bu(t)CHO, PhCHO, (CH₂)₅CO and PhCOMe] at the same temperature leads, after hydrolysis with water to the expected chiral 1,3-diols 3. The same methodology applied to both (R) and (S) protected epoxyalcohols 4 yields the expected enantiomerically pure compounds 6 and 7, which are monoprotected 1,2,4-triols; carbonation of these last two starting materials affords hydroxyacids 6d and 7d.