The reaction shown above involves a fairly challenging rearrangement to form an oxazolidine product.
Click the hints below to get started.
Hint 1: Fragment Mapping
In mapping fragments from reactant to product, it appears as though the five-carbon chain is still intact.
Hint 2: What can be protonated?
Although the amine is the stronger base, protonation of the epoxide kicks off the reaction.
We now have an electrophile and three potential nucleophiles. What are the potential nucleophiles?
Hint 3: A Key Bond
A key bond that needs to be formed is from the aromatic ring to the allylic carbon. Once the epoxide is protonated, it can open up to give an allylic carbocation.
