Sharpless epoxidation NaOH, C,H5SH OH Y (+)-DET H,0, (CH3),COH SC&H5 HO OH

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
Section11.SE: Something Extra
Problem 40AP: The following Walden cycle has been carried out. Explain the results, and indicate where Walden...
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Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment
of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify
the structure of Y and draw a mechanism for the conversion of Y to Z.
Account for the stereochemistry of the stereogenic centers in Z. Z has
been used as an intermediate in the synthesis of chiral carbohydrates.

Sharpless
epoxidation
NaOH, C,H5SH
OH
Y
(+)-DET
H,0, (CH3),COH
SC&H5
HO
OH
Transcribed Image Text:Sharpless epoxidation NaOH, C,H5SH OH Y (+)-DET H,0, (CH3),COH SC&H5 HO OH
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