Sharpless epoxidation can be used to stereoselectively convert an allylic alcohol to an epoxy alcohol using Ti(O/Pr)4, t-butyl hydroperoxide (TBHP) and a chiral diethyl tartrate (DET), as exemplified in the formation of compound E below. HO. OBn Ti(O/Pr)4 TBHP L-(+)-DET CH₂Cl₂ HO E OBn

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.34P: Treating 4-penten-1-ol with bromine in water forms a cyclic bromoether. Account for the formation of...
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E can be readily debenzylated to give a diol structure, is the diol chiral? Explain.

Sharpless epoxidation can be used to stereoselectively convert an allylic alcohol to an
epoxy alcohol using Ti(O/Pr)4, t-butyl hydroperoxide (TBHP) and a chiral diethyl tartrate
(DET), as exemplified in the formation of compound E below.
HO.
OBn
Ti(O/Pr)4
TBHP
L-(+)-DET
CH₂Cl₂
HO
E
OBn
Transcribed Image Text:Sharpless epoxidation can be used to stereoselectively convert an allylic alcohol to an epoxy alcohol using Ti(O/Pr)4, t-butyl hydroperoxide (TBHP) and a chiral diethyl tartrate (DET), as exemplified in the formation of compound E below. HO. OBn Ti(O/Pr)4 TBHP L-(+)-DET CH₂Cl₂ HO E OBn
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