The following is an example of a reaction sequence developed by Derin C. DAmico and
Chapter 18, Problem 18.35(choose chapter or problem)
The following is an example of a reaction sequence developed by Derin C. DAmico and Michael E. Jung (UCLA) that results in enantiospecific formation of two new chirality centers and a carboncarbon bond. The sequence includes a HornerWadsworthEmmons reaction (Section 16.10B), a Sharpless asymmetric epoxidation (Section 11.13), and a novel rearrangement that ultimately leads to the product. Propose a mechanism for rearrangement of the epoxy alcohol under the conditions shown to form the aldol product. [Hint: The rearrangement can also be accomplished by preparing a trialkylsilyl ether from the epoxy alcohol in a separate reaction first and then treating the resulting silyl ether with a Lewis acid catalyst (e.g., BF3).]
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