Journal of Organic Chemistry p. 5396 - 5398 (1983)
Update date:2022-08-29
Topics:
Robinson, Philip L.
Barry, Carey N.
Bass, S. Woody
Jarvis, Susan E.
Evans, Slayton A.
The regioselectivity of cyclodehydration of chiral diols has been examined with the reagents diethoxytriphenylphosphorane, triphenylphosphine-tetrachloromethane-potassium carbonate, and triphenylphosphine-diethyl azodicarboxylate. (S)-(+)-Propane-1,2-diol and (R)-(-)-pentane-1,4-diol afford 80-87percent retention of stereochemistry at the chiral carbon in the ether while (S)-(+)-phenylethane-1,2-diol affords essentially racemic styrene oxide with all three reagents.
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Doi:10.1002/anie.201410796
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