Tetrahedron Letters p. 6943 - 6946 (1991)
Update date:2022-08-04
Topics:
Guanti
Banfi
Narisano
Thea
Asymmetrized 2-alkenyl 1,3-propanediols are stereoselectively epoxidized to the same main diastereoisomer both with 3-chloroperbenzoic acid and the VO(acac)2/t-butyl hydroperoxyde system. Using the latter epoxidating reagent in combination with a protection-deprotection sequence involving the two homoallylic hydroxy groups, all the four cis epoxides were easily achieved in stereoisomeric pure from starting from a single common (Z) precursor.
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