Chapter 17.9, Problem 11P

Interpretation Introduction

Interpretation:

The absolute configuration of the $2,3$ -epoxy- $1$ -hexanol produced in the mentioned reaction if diethyl $\left(2S,3S\right)$ -tartrate were used instead of $\left(2R,3R\right)$ is to be determined.

Concept Introduction:

>

Sharpless epoxidation involves the oxidation of double bond between carbon atoms to form an epoxide.

>

This oxidation occurs only in allylic alcohol. This is an enantioselective oxidation, which means predominantly one enantiomer is formed.

>

Sharpless reagents are tert-butyl hydroperoxide, ${\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}\text{COOH}$; titanium $\left(\text{IV}\right)$ iso-propoxide, $\text{Ti}{\left[\text{OCH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\right]}_{\text{4}}$; and diethyl tartrate.