X-Nico

unusual facts about protecting group



Vinyl iodide functional group

Vilarrasa and Costa’s group hypothesized that radical reactions producing HI and I2 help facilitate cleavage in alcohol’s protecting group and may add into other alkene bonds.


see also

Kuwajima Taxol total synthesis

Palladium on carbon hydrogenation removed the benzyl protecting group allowing the Swern oxidation of 2.10 to ketone 2.11

Orthoester

Another example is the bicyclic OBO protecting group (4-methyl-2,6,7-trioxa-bicyclo2.2.2octan-1-yl) which is formed by the action of (3-methyloxetan-3-yl)methanol on activated carboxylic acids in the presence of Lewis acids and was developed by Elias James Corey.