The waters around the islands are crystal clear and full of aquatic life. Though the waters are clear, the rationale behind the reaction of molecule 60 to molecule 61 may not be so clear.
✖ Provide a rationale for the diastereoselectivity of this reaction.
The molecule is deprotonated by a large base, producing an enolate. This enolate then attacks the methyl iodide in a SN2 reaction, producing our molecule. The reason for this preference is due to the sterically hindered approach when entering from the front side of the molecule. The chances of the methyl iodide approaching from the back to react are much greater, as the face of the enolate is clear from that side.
