Our Plan

Carson was heavily questioned about the specifics of how his plan would come to fruition.  Confident and creepy, Carson answered, “My own personal theory is that Joseph built the pyramids to protect grain . . . and in a similar manner, Cbz was created to protect Nitrogen groups.”  Carson went on to detail the mechanism of deprotection and hydrogenation with a helpful gif.



Our mechanism consisted of two parts.  First, the hydrogenation, and second, the deprotection of the nitrogen group and removal of Cbz. In the first step of this mechanism, there is a hydrogenation of a carbon-carbon double bond to provide syn addition. This addition was selected specifically for this double bond due to the resonance stabilization of the nitrogens and the protecting group on the lone nitrogen on the end of the carbon chain. The end product resulted in the methyl and ester groups facing the same direction.


deprotect

The second part of the reaction consisted of removing a protecting group through the use of the rhodium catalyst. The Cbz was deprotected to give the final product of the two step reaction. The nitrogen group remained on the end of the carbon chain as a positively charged atom with the formic acid anion.

mechanism