Chapter 12, Problem 12.59P

Interpretation Introduction

(a)

Interpretation: The allylic alcohol and $\text{DET}$ isomer needed to make the given chiral epoxide using Sharpless asymmetric epoxidation reaction is to be identified.

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

Interpretation Introduction

(b)

Interpretation: The allylic alcohol and $\text{DET}$ isomer needed to make the given chiral epoxide using Sharpless asymmetric epoxidation reaction is to be identified.

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

Interpretation Introduction

(c)

Interpretation: The allylic alcohol and $\text{DET}$ isomer needed to make the given chiral epoxide using Sharpless asymmetric epoxidation reaction is to be identified.

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