Chapter 11, Problem 11.28P

Interpretation Introduction

Interpretation:

Using Sharpless epoxidation, the allylic alcohol that can be used to prepare the given enantiomer has to be shown.

Concept Introduction:

Sharpless asymmetric epoxidation: Titanium-catalyzed asymmetric epoxidation of primary allylic alcohols is proposed by the Barry Sharpless known as Sharpless epoxidation. The reagent consists of tert-butyl hydroperoxide, titanium tetraisoproxide $\left[\text{Ti}{\left(\text{O-iPr}\right)}_{\text{4}}\right]$ and the diethyl tartrate.

Sharpless epoxidation is stereospecific based on the diethyl tartrate $\left(\text{DET}\right)$ added. If the $-\left(\text{DET}\right)$ enantiomer is used, that catalyzes the reaction and delivers the epoxide Oxygen from the top face of the alkene; the $+\left(\text{DET}\right)$ enantiomer is used, that delivers the epoxide where the oxygen is attached from the bottom of the alkene.