CHIRAL BETA-OXIDOFUNCTIONALISED ORGANOLITHIUM COMPOUNDS FROM EPOXIDES- EPC-SYNTHESIS OF 1,3-DIOLS

The reductive opening of (S)-propylene oxide (I) with lithium powder a nd a catalytic amount of DTBB (5 mol %) in THF at -78 degrees C follow ed by treatment with different carbonyl compounds [Bu(t)CHO, PhCHO, (C H2)(5)CO and PhCOMe] at the same temperature leads, after hydrolysis w ith water to the expected chiral 1,3-diols 3. The same methodology app lied to both (R) and(S) protected epoxyalcohols 4 yields the expected enantiomerically pure compounds 6 and 7, wich are monoprotected 1,2,4- triols; carbonation of these last two starting materials affords hydro xyacids 6d and 7d.