Tetrahedron Asymmetry p. 1907 - 1910 (1995)
Update date:2022-08-16
Topics:
Bachki
Foubelo
Yus
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.
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Doi:10.1039/jr9510000522
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