Q.57.
Question
Question: Draw the product of each asymmetric epoxidation reaction.
Step-by-Step Solution
Verified Answer
Answer
1Step 1: Asymmetric epoxidation
- Asymmetric epoxidation is also known as Sharpless epoxidation.
- Allyl alcohols participate in this reaction.
- DET affects the stereochemistry of the product.If it is of (+)-DET, then the epoxide is formed below the plane, and if it is (-)-DET, then the epoxide is formed above the plane.
2Step 2: Products of the given reaction
The double bond of the alkene reacts with the sharpless reagent and forms the epoxide.
The specialty of the reaction is that it forms one of the stereoisomers in excess. Hence, the selective product can be obtained by using a suitable reagent.
The formation of products for the given reactions is shown below.
Other exercises in this chapter
Q.55.
Question: DHA is a fatty acid derived from fish oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3CH22OCO2H]&n
View solution Q.56.
Question: One compound that contributes to the “seashore smell”at beaches in Hawai’s is dictyopterene D’ with excess H2 in the pres
View solution Q.58.
Question: Epoxidation of the following allylic alcohol using the Sharpess reagent (-)-DET gives two epoxy alcohols in a ratio of 87:13.Assign structures to the
View solution Q.59.
Question: What allylic alcohol and DET isomer are needed to make each chiral epoxide using a sharpless asymmetric epoxidation reaction?
View solution