Sharpless epoxidation NaOH, CH;SH OH (+)-DET H,0, (CH2);COH .SCH5 х он

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter24: Carboxylic Acids & Derivatives
Section: Chapter Questions
Problem 12CTQ
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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, CH;SH
OH
(+)-DET
H,0, (CH2);COH
.SCH5
х
он
Transcribed Image Text:Sharpless epoxidation NaOH, CH;SH OH (+)-DET H,0, (CH2);COH .SCH5 х он
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