We are members of the Chem 215HH class taught at the University of Michigan taught by Melanie Sanford.

Leading Question

What is the function and purpose of the protecting group for this reaction?


The protecting group eliminates the possibility of acid/base chemistry occurring at that site.  This is crucial because, was the protecting group not there, the reagents in the second step would deprotonate the wrong carbon and the reaction would not proceed correctly. It is likely that, upon deprotonation, the oxygen in question would become involved in a series of side reactions that would change the configuration of the molecule. 

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This paper provides an analogous transformation where this process occurs: Abe, H.; Ito, Y.; Saneyoshi, H.; Abe, H. Hatano, K. Mashimo, T. Tetrahedron Lett. 2013, 54, 1080-1083. 

A picture of the deprotonation that would occur is shown below:

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